Hydrochloric Acid → t-butyl 7-(N-benzyloxycarbonylamino)-3-hydroxy-2-phenylheptanoate

HRID 2392932Notes

Reaction equation

HRID 2392932 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:31])[CH:17]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([OH:31])[CH:17]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 53889532t-butyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-phenylheptanoate

Product 1

HCID 18980752t-butyl 7-(N-benzyloxycarbonylamino)-3-hydroxy-2-phenylheptanoateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The same procedures as in Example 26 were performed except that 0.2 g (0.47 mmol) of t-butyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-phenylheptanoate instead of ethyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-phenylheptanoate was dissolved in 4 ml of methanol, 18 mg (0.47 mol) of sodium borohydride was added, and 4 ml of 4N hydrochloric acid was added to the reaction solution, to prepare the target compound as a pale yellow oil in an amount of 196 mg at a yield of 98%. The selectivity of the products in terms of the ratio of the syn-form to the anti-form was 7:3. The analytical results on the target compound are given below.

Workup

  1. customThe analytical results on the target compound

Sources & evidence

ORD record
ord-28de9f1fcdc54cb18ab30f4f090a4c73
Source dataset
uspto-grants-1998_09
Patent number
US05801271

Reaction notes

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