Imidazole → HCID 22874313, compound

HRID 1377172Notes

Reaction equation

HRID 1377172 reaction equation
[C:1]([NH:8][C@@H:9]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C@@H:10]([OH:25])[CH2:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)[C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:33]([Si:37]([CH3:40])([CH3:39])Cl)([CH3:36])([CH3:35])[CH3:34].N1C=CN=C1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C1COCC1.CO>[C:1]([NH:8][C@@H:9]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C@@H:10]([O:25][Si:37]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:40])[CH3:39])[CH2:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[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 22874290HCID 22874290, compound

Product 1

HCID 22874313HCID 22874313, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In analogy with Example 44e), 1.3 g of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-[(3-methoxyphenyl)methyl]hexanoic acid in 13 ml of DMF are silylated with 1.987 g of tert-butyldimethylchlorosilane and 1.646 g of imidazole. The silyl ester group in the crude product is detached at RT in 2 h in a mixture consisting of 38.94 ml of methanol, 13.34 ml of THF, 13.34 ml of water and 2.35 g of potassium carbonate. Chromatography on silica gel (eluents: E, D and C) yields the pure title compound. TLC Rf (D)=0.06. FAB-MS (M+H)+ =558.

Sources & evidence

ORD record
ord-4b1bb17f1ba845cba73ed87c60d5ebf8
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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