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1-Hydroxybenzotriazole → Oritavancin

HRID 1397132
Notes
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Reaction equation

HRID 1397132 reaction equation
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:113]3[CH:114]=[CH:115][C:110](=[C:111]([Cl:116])[CH:112]=3)[O:109][C:37]3=[C:38]([O:73][C@@H:74]4[O:79][C@H:78]([CH2:80][OH:81])[C@@H:77]([OH:82])[C@H:76]([OH:83])[C@H:75]4[O:84][C@@H:85]4[O:90][C@@H:89]([CH3:91])[C@H:88]([OH:92])[C@:87]([NH:94][CH2:95][C:96]5[CH:101]=[CH:100][C:99]([C:102]6[CH:107]=[CH:106][C:105]([Cl:108])=[CH:104][CH:103]=6)=[CH:98][CH:97]=5)([CH3:93])[CH2:86]4)[C:39]4[O:41][C:42]5[CH:47]=[CH:46][C:45]([C@@H:48]([OH:71])[C@@H:49]([NH:61][C:62]([C@H:64]([NH:69][CH3:70])[CH2:65][CH:66]([CH3:68])[CH3:67])=[O:63])[C:50]([NH:52][C@@H:53]([CH2:57][C:58]([NH2:60])=[O:59])[C:54]([NH:56][C@H:34]([C:35]([CH:40]=4)=[CH:36]3)[C:32](=[O:33])[NH:31][C@H:27]3[C:28]([NH:30][C@@H:10]2[C:11]([NH:13][C@H:14]([C:120]([OH:122])=[O:121])[C:15]2[C:20]([C:21]4[CH:26]=[C:25]3[CH:24]=[CH:23][C:22]=4[OH:117])=[C:19]([OH:118])[CH:18]=[C:17]([OH:119])[CH:16]=2)=[O:12])=[O:29])=[O:55])=[O:51])=[CH:44][C:43]=5[Cl:72])[CH2:5][C@@:4]([NH2:124])([CH3:123])[C@H:3]1[OH:125].OP(O)(O)=O.OP(O)(O)=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CN(C)CCN(C)C(=O)CO>CS(C)=O.CN(C=O)C.C(OCC)C>[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@@H:10]3[NH:30][C:28](=[O:29])[C@@H:27]([C:25]4[CH:24]=[CH:23][C:22]([OH:117])=[C:21]([C:20]5[C:19]([OH:118])=[CH:18][C:17]([OH:119])=[CH:16][C:15]=5[C@@H:14]([C:120]([OH:122])=[O:121])[NH:13][C:11]3=[O:12])[CH:26]=4)[NH:31][C:32](=[O:33])[C@H:34]3[C:35]4=[CH:40][C:39]([O:41][C:42]5[CH:47]=[CH:46][C:45]([C@@H:48]([OH:71])[C@@H:49]([NH:61][C:62]([C@H:64]([NH:69][CH3:70])[CH2:65][CH:66]([CH3:67])[CH3:68])=[O:63])[C:50]([NH:52][C@@H:53]([CH2:57][C:58]([NH2:60])=[O:59])[C:54]([NH:56]3)=[O:55])=[O:51])=[CH:44][C:43]=5[Cl:72])=[C:38]([O:73][C@@H:74]3[O:79][C@H:78]([CH2:80][OH:81])[C@@H:77]([OH:82])[C@H:76]([OH:83])[C@H:75]3[O:84][C@@H:85]3[O:90][C@@H:89]([CH3:91])[C@H:88]([OH:92])[C@:87]([NH:94][CH2:95][C:96]5[CH:97]=[CH:98][C:99]([C:102]6[CH:103]=[CH:104][C:105]([Cl:108])=[CH:106][CH:107]=6)=[CH:100][CH:101]=5)([CH3:93])[CH2:86]3)[C:37](=[CH:36]4)[O:109][C:110]3=[C:111]([Cl:116])[CH:112]=[C:113]2[CH:114]=[CH:115]3)[CH2:5][C@@:4]([NH2:124])([CH3:123])[C@H:3]1[OH:125]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53297457Oritavancin DiphosphateHCID 54488530N-(2-(Dimethylamino)ethyl)-2-Hydroxy-N-methylacetamide

Product 1

HCID 16136912Oritavancin

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

Oritavancin diphosphate 5 (630.7 mg, 0.3171 mmol), HBTU (601.1 mg, 1.585 mmol) and HOBt (173.4 mg, 1.283 mmol) was dissolved in the mixture of DMSO (4 mL) and DMF (8 mL) and 0.4 mL (2.296 mmol) of DIPEA was added. After stirring at room temperature for 30 min, the solution of 102 in 1 mL DMF was added plus 1 mL rinse. A yellow clear solution was obtained. After 2 days, 250 mL of diethyl ether was added to the reaction while stirring. After stand for a few min, the clear solution was decanted. The process was repeated with another 150 mL of diethyl ether. The residual mixture was dried in vacuo. The product was purified on repetitive C18 flash columns on a Biotage automatic chromatography system with gradient elution of H3PO4 (30 mM)-triethylamine (20 mM) buffer (aq, pH3)/methanol and then C18 column on Biotage system with gradient elution of 0.1% formic acid buffer (aq, pH2)/methanol. The purified product is a white solid as penta-formate salt (43.2 mg, 6%): ESI-MS calculated for C93H111Cl3N12O27: calculated 484.8 (M/4+H), 646.1 (M/3+H), 967.6 (M/2+H). found: 484.6, 646.0, 967.6.

Workup

  1. additionwas added
  2. washrinse
  3. customA yellow clear solution was obtained
  4. waitAfter 2 days
  5. stirringwhile stirring
  6. customAfter stand for a few min, the clear solution was decanted
  7. customThe residual mixture was dried in vacuo
  8. customThe product was purified on repetitive C18 flash columns on a Biotage automatic chromatography system with gradient elution of H3PO4 (30 mM)-triethylamine (20 mM) buffer (aq, pH3)/methanol
  9. washC18 column on Biotage system with gradient elution of 0.1% formic acid buffer (aq, pH2)/methanol

Sources & evidence

ORD record
ord-c6f2724223b84a21bfe9883bcfe2c70a
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08901072B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes