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

HRID 263770Notes

Reaction equation

HRID 263770 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]([C:23]#[N: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.CO.C1COCC1.O.C(OCC)(=O)C.CCCCCC>[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]([C:23]#[N:24])[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 228742915(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(m-cyanophenylmethyl)-hexanoic acid

Product 1

HCID 228743155(S)-(Boc-amino)-4(S)-(tert-butyldimethylsilyloxy)-6-phenyl-2(R)-(m-cyanophenylmethyl)-hexanoic acid

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Analogously to Example 1j), 1.4 g (3.2 mmol) of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(m-cyanophenylmethyl)-hexanoic acid in 20 ml of DMF are silylated with 2.2 g (14.6 mmol) of tert-butyldimethylchlorosilane and 1.8 g (26 mmol) of imidazole. Hydrolysis of the silyl ester function with 2.6 g of potassium carbonate in 55 ml of methanol/THF/water 8:1:2, followed by column chromatography (SiO2, ethyl acetate/hexane 1:1), yields the title compound: TLC Rf (A)=0.39; tRet (I)=19.8 min.

Sources & evidence

ORD record
ord-542f31d18d8841e4ad78b13636fbecd1
Source dataset
uspto-grants-1997_07
Patent number
US05643878

Reaction notes

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