Diisopropylethylamine → HCID 86597506, compound

HRID 2055062Notes

Reaction equation

HRID 2055062 reaction equation
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([O:15][C:16]3[C:17]4[O:71][C:67]5=[C:68]([Cl:70])[CH:69]=[C:64]([CH:65]=[CH:66]5)[C@@H:63]([OH:72])[C@@H:62]5[NH:73][C:74](=[O:75])[C@@H:43]([C:44]6[CH:45]=[CH:46][C:47]([OH:79])=[C:48]([C:50]7[C:55]([OH:56])=[CH:54][C:53]([OH:57])=[CH:52][C:51]=7[C@@H:58]([C:76]([OH:78])=[O:77])[NH:59][C:60]5=[O:61])[CH:49]=6)[NH:42][C:40](=[O:41])[C@H:39]5[C:19](=[CH:20][C:21]=3[O:22][C:23]3[CH:24]=[CH:25][C:26]([C@@H:30]([OH:94])[C@@H:31]([NH:84][C:85]([C@H:87]([NH:92][CH3:93])[CH2:88][CH:89]([CH3:91])[CH3:90])=[O:86])[C:32]([NH:34][C@@H:35]([CH2:80][C:81]([NH2:83])=[O:82])[C:36]([NH:38]5)=[O:37])=[O:33])=[CH:27][C:28]=3[Cl:29])[CH:18]=4)[O:13][C@H:12]([CH2:95][OH:96])[C@@H:11]([OH:97])[C@@H:10]2[OH:98])[CH2:5][C@@:4]([NH2:100])([CH3:99])[C@@H:3]1[OH:101].Cl.Cl.[CH3:104][O:105]C(=O)CN.C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CS(C)=O.O.CO.C(Cl)(Cl)Cl.CN(C=O)C>[CH3:104][O:105][NH:59][CH2:58][C:76]([OH:78])=[O:77].[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([O:15][C:16]3[C:17]4[O:71][C:67]5=[C:68]([Cl:70])[CH:69]=[C:64]([CH:65]=[CH:66]5)[C@@H:63]([OH:72])[C@@H:62]5[NH:73][C:74](=[O:75])[C@@H:43]([C:44]6[CH:45]=[CH:46][C:47]([OH:79])=[C:48]([C:50]7[C:55]([OH:56])=[CH:54][C:53]([OH:57])=[CH:52][C:51]=7[C@@H:58]([C:76]([OH:78])=[O:77])[NH:59][C:60]5=[O:61])[CH:49]=6)[NH:42][C:40](=[O:41])[C@H:39]5[C:19](=[CH:20][C:21]=3[O:22][C:23]3[CH:24]=[CH:25][C:26]([C@@H:30]([OH:94])[C@@H:31]([NH:84][C:85]([C@H:87]([NH:92][CH3:93])[CH2:88][CH:89]([CH3:90])[CH3:91])=[O:86])[C:32]([NH:34][C@@H:35]([CH2:80][C:81]([NH2:83])=[O:82])[C:36]([NH:38]5)=[O:37])=[O:33])=[CH:27][C:28]=3[Cl:29])[CH:18]=4)[O:13][C@H:12]([CH2:95][OH:96])[C@@H:11]([OH:97])[C@@H:10]2[OH:98])[CH2:5][C@@:4]([NH2:100])([CH3:99])[C@@H:3]1[OH:101]

Participants

10

Reactant 4

HCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 6420023Vancomycin monohydrochlorideHCID 22988621HOBt HBTU

Product 1

HCID 86597506HCID 86597506, compound

Reagents, catalysts & solvents 5

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Vancomycin hydrochloride (317 mg, 0.213 mmol) and glycine methyl ester hydrochloride (54 mg, 0.426 mmol) are dissolved in 2 mL DMSO and 2 mL DMF and stirred at 0° C. Diisopropylethylamine (186 μL, 0.3195 mmol) is added to the reaction vessel via syringe followed by HOBt/HBTU (710 μL 0.45M DMF solution, 0.319 mmol). The ice bath is removed after addition. After 10 minutes, the reaction is completed and the reaction solution is directly loaded to a poly(divinylbenzene) column (30 mm×8 cm, 50-100 micron particle size) and eluted with methanol/water (0, 10%, 20%, 30%, 40%, 50% of 100 mL each). The fractions containing the pure products are combined and evaporated to give 249 mg of (CXXIX) as a white powder, 77%. Rf=0.15 (CHCl3:MeOH:H2O=3:2:0.5). Mass Spec. [M+H]+, 1521; [M−V]+, 1377.

Workup

  1. customThe ice bath is removed
  2. additionafter addition
  3. washeluted with methanol/water (0, 10%, 20%, 30%, 40%, 50% of 100 mL each)
  4. additionThe fractions containing the pure products
  5. customevaporated
  6. customto give 249 mg of (CXXIX) as a white powder, 77%

Sources & evidence

ORD record
ord-9585e905fcf346529f672770479ae0b2
Source dataset
uspto-grants-2008_02
Patent number
US07331920B2

Reaction notes

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