Imidazole → 5(S)-(Boc-amino)-4(S)-(tert-butyldimethylsilyloxy)-6-phenyl-2(R)-(m-fluorophenylmethyl)-hexanoic acid

HRID 263786Notes

Reaction equation

HRID 263786 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]=[C:19]([F:23])[CH:18]=1)[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:27]=[CH:28][CH:29]=[CH:30][CH:31]=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]=[C:19]([F:23])[CH:18]=1)[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 228742925(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(m-fluorophenylmethyl)-hexanoic acid

Product 1

HCID 228743165(S)-(Boc-amino)-4(S)-(tert-butyldimethylsilyloxy)-6-phenyl-2(R)-(m-fluorophenylmethyl)-hexanoic acid

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Analogously to Example 1j), 2.7 g (6.25 mmol) of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(m-fluorophenylmethyl)-hexanoic acid in 30 ml of DMF are silylated with 4.33 g (28.8 mmol) of tert-butyldimethylchlorosilane and 3.51 g (51.3 mmol) of imidazole. Hydrolysis of the silyl ester function with 5.1 g of potassium carbonate in 100 ml of methanol/THF/water 4:1:1 yields the title compound after column chromatography (SiO2, hexane/ethyl acetate 2:1): tRet (I)=20.8 min.

Sources & evidence

ORD record
ord-f9a60a54fd9f4e9ab4bf890e251032db
Source dataset
uspto-grants-1997_07
Patent number
US05643878

Reaction notes

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