Triethylamine → HCID 86613021, compound

HRID 731164Notes

Reaction equation

HRID 731164 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:25]([C@@H:28]([CH2:46][C@H:47]([CH2:51][C:52]1[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[C:54]([O:60][CH2:61][CH2:62][CH2:63][O:64][CH3:65])[CH:53]=1)[CH:48]([CH3:50])[CH3:49])[C@@H:29]([O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[CH2:30][C@@H:31]([CH:35]([CH3:37])[CH3:36])[C:32](O)=[O:33])=[N+:26]=[N-:27].[NH2:66][CH2:67][CH2:68][N:69]1[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]1.CCN(CC)CC>CC#N.CCOC(C)=O>[N:69]1([CH2:68][CH2:67][NH:66][C:32](=[O:33])[C@H:31]([CH:35]([CH3:37])[CH3:36])[CH2:30][C@H:29]([O:38][Si:39]([C:42]([CH3:45])([CH3:43])[CH3:44])([CH3:40])[CH3:41])[C@@H:28]([N:25]=[N+:26]=[N-:27])[CH2:46][C@H:47]([CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[C:54]([O:60][CH2:61][CH2:62][CH2:63][O:64][CH3:65])[CH:53]=2)[CH:48]([CH3:49])[CH3:50])[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 33944N-(2-Aminoethyl)piperidineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57619557HCID 57619557, compound

Product 1

HCID 86613021HCID 86613021, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

HBTU (1.20 g, 3.0 mmol) was added to a solution of (2S,4S,5S,7S)-5-azido-4-(tert-butyl-dimethyl-silanyloxy)-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (1.50 g, 2.5 mmol) in CH3CN (50 mL). Then 2-aminoethylpiperidine (324 mg, 2.5 mmol) and NEt3 (3.9 mL) were added and the resulting solution was stirred at RT for 2.5 hours. For workup, EtOAc was added and the organic phase was washed with 1 N HCl, saturated NaHCO3 solution and brine. Drying of the organic phase (Na2SO4) and evaporation of the solvent affords the crude product which is purified by flash column chromatography [CH2Cl2:MeOH (95:5)] to give the desired product as a colorless oil. MS (LC-MS): 705.1 [M+H]+; tR (HPLC, C18 column, 10-100% CH3CN/H2O/5 minutes, 100% CH3CN/3 minutes, 100-10% CH3CN/H2O/3 minutes, flow: 1.5 mL/min.): 6.82 minutes.

Workup

  1. washthe organic phase was washed with 1 N HCl, saturated NaHCO3 solution and brine
  2. dry with materialDrying of the organic phase (Na2SO4) and evaporation of the solvent
  3. customaffords the crude product which
  4. customis purified by flash column chromatography [CH2Cl2:MeOH (95:5)]

Sources & evidence

ORD record
ord-116d6d472a794b02bbfd9a9481b5e765
Source dataset
uspto-grants-2009_09
Patent number
US07582782B2

Reaction notes

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