Imidazole → HCID 22874311, compound

HRID 1377178Notes

Reaction equation

HRID 1377178 reaction equation
[C:1]([NH:8][C@@H:9]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@@H:10]([OH:29])[CH2:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=1)[C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:37]([Si:41]([CH3:44])([CH3:43])Cl)([CH3:40])([CH3:39])[CH3:38].N1C=CN=C1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C1COCC1.CO>[C:1]([NH:8][C@@H:9]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@@H:10]([O:29][Si:41]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:44])[CH3:43])[CH2:11][C@@H:12]([CH2:16][C:17]1[CH:18]=[C:19]([O:27][CH3:28])[C:20]([O:25][CH3:26])=[C:21]([O:23][CH3:24])[CH:22]=1)[C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

9

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 28928tert-Butyldimethylsilyl chlorideHCID 22874288HCID 22874288, compound

Product 1

HCID 22874311HCID 22874311, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In analogy with Example 44e), 1.526 g of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-[(3,4,5-trimethoxyphenyl)methyl]hexanoic acid in 15.16 ml of DMF are silylated with 2.11 g of tert-butyldimethylchlorosilane and 1.683 g of imidazole. The silyl ester group in the crude product is detached, at RT in 2.5 h, in a mixture consisting of 40.3 ml of methanol, 13.8 ml of THF, 13.8 ml of water and 2.42 g of potassium carbonate. The title compound is purified by being chromatographed twice on silica gel (solvents: hexane, C and J). TLC Rf (A)=0.39. FAB-MS (M+H)+ =618.

Workup

  1. customThe title compound is purified
  2. customby being chromatographed twice on silica gel (solvents: hexane, C and J)

Sources & evidence

ORD record
ord-0ac42789d77549c79bd6de26713f8c4e
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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