Imidazole → HCID 22874319, compound

HRID 263767Notes

Reaction equation

HRID 263767 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]=[CH:19][C:18]=1C#N)[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].[NH:41]1C=CN=[CH:42]1.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:32]=[CH:31][CH:30]=[CH:29][CH:28]=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][C:20]([C:42]#[N:41])=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 28928tert-Butyldimethylsilyl chlorideHCID 22874293HCID 22874293, compound

Product 1

HCID 22874319HCID 22874319, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Analogously to Example 1j), 0.85 g (1.93 mmol) of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(o-cyanophenylmethyl)-hexanoic acid in 10 ml of DMF are silylated with 1.34 g (8.9 mmol) of tert-butyldimethylchlorosilane and 1.08 g (15.9 mmol) of imidazole. Hydrolysis of the silyl ester function with 1.6 g of potassium carbonate in 40 ml of methanol/THF/water 5:1:2, followed by column chromatography (SiO2, ethyl acetate/hexane 1:1), yields the title compound: TLC Rf (A)=0.4; tRet (I)=20.0 min.

Sources & evidence

ORD record
ord-a47c66228a8d4c1c9aeef14bb8e086f7
Source dataset
uspto-grants-1997_07
Patent number
US05643878

Reaction notes

Loading…