Imidazole → 5(S)-(Boc-Amino)-4(S)-(tert-butyldimethylsilyloxy)-6-phenyl-2(R)-[(o-fluorophenyl)methyl]hexanoic acid

HRID 2394089Notes

Reaction equation

HRID 2394089 reaction equation
[C:1]([NH:8][C@@H:9]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@@H:10]([OH:24])[CH2:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])[C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:32]([Si:36]([CH3:39])([CH3:38])Cl)([CH3:35])([CH3:34])[CH3:33].N1C=CN=C1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CO.C1COCC1.O.CCCCCC.C(OCC)(=O)C>[C:1]([NH:8][C@@H:9]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@@H:10]([O:24][Si:36]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:39])[CH3:38])[CH2:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])[C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 28928tert-Butyldimethylsilyl chlorideHCID 228742945(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(o-fluorophenylmethyl)-hexanoic acid

Product 1

HCID 228743185(S)-(Boc-Amino)-4(S)-(tert-butyldimethylsilyloxy)-6-phenyl-2(R)-[(o-fluorophenyl)methyl]hexanoic acid

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

In analogy with Example 1j), 1.5 g (3.47 mmol) of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-[(o-fluorophenyl)methyl]hexanoic acid in 15 ml of DMF are silylated with 2.4 g (16 mmol) of tert-butyldimethylchlorosilane and 1.95 g (28.5 mmol) of imidazole. Hydrolysis of the silyl ester function with 2.8 g of potassium carbonate in 50 ml of methanol/THF/water, 4:1:1, yields the title compound after column chromatography (SiO2, hexane/ethyl acetate, 2:1): TLC Rf (D)=0.33; tRet (II)=20.7 min.

Sources & evidence

ORD record
ord-eafef1b559b74800b7cbf72b624840b3
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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