Imidazole → HCID 22874312, compound

HRID 2394129Notes

Reaction equation

HRID 2394129 reaction equation
[C:1]([NH:8][C@@H:9]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@@H:10]([OH:27])[CH2:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)[C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:35]([Si:39]([CH3:42])([CH3:41])Cl)([CH3:38])([CH3:37])[CH3:36].N1C=CN=C1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C1COCC1.CO>[C:1]([NH:8][C@@H:9]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@@H:10]([O:27][Si:39]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:42])[CH3:41])[CH2:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=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 22874289HCID 22874289, compound

Product 1

HCID 22874312HCID 22874312, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In analogy with Example 44e), 804 mg of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-[(3,4-dimethoxyphenyl)methyl]hexanoic acid in 5.94 ml of DMF are silylated with 1.162 g of tert-butyldimethylchlorosilane and 946.6 mg of imidazole. The silyl ester in the crude product is cleaved at RT in 2 h in a mixture consisting of 19.61 ml of methanol, 7.56 ml of THF, 7.56 ml of water and 1.334 g of potassium carbonate. The title compound is purified by being chromatographed twice on silica gel (eluents: D, C, J and B). TLC Rf (C)=0.27. MS M+ =557.

Workup

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

Sources & evidence

ORD record
ord-6dc7307d90354d08b4559ef0836d3f7b
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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