Imidazole → HCID 22876421, compound

HRID 1377141Notes

Reaction equation

HRID 1377141 reaction equation
[C:1]([NH:8][C@@H:9]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C@@H:10]([OH:35])[CH2:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH2:26][C:27]2[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:34])(=[O:25])=[O:24])=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:43]([Si:47]([CH3:50])([CH3:49])Cl)([CH3:46])([CH3:45])[CH3:44].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]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C@@H:10]([O:35][Si:47]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:50])[CH3:49])[CH2:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH2:26][C:27]2[C:28]([Cl:34])=[CH:29][CH:30]=[CH:31][C:32]=2[Cl:33])(=[O:25])=[O:24])=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

10

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 28928tert-Butyldimethylsilyl chlorideHCID 22876407HCID 22876407, compound

Product 1

HCID 22876421HCID 22876421, compound

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

In analogy with Example 5f), 5.0 g (7.85 mmol) of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-{[p-(2,6-dichlorobenzylsulfonyl)phenyl]methyl}hexanoic acid in 74 ml of DMF are silylated with 5.4 g (36.1 mmol) of tert-butyldimethylchlorosilane and 4.4 g (64.4 mmol) of imidazole. Hydrolysis of the silyl ester function with 6.5 g of potassium carbonate in 85 ml of methanol, 22 ml of THF and 22 ml of water yields the title compound after column chromatography (SiO2, hexane/ethyl acetate, 1:1) and stirring-up with DIPE: TLC Rf (C)=0.5; tRet (II)=21.0 min.

Sources & evidence

ORD record
ord-044b7c62030d44baa68955c44da47368
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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