Sodium borohydride → HCID 14037152, compound

HRID 654060Notes

Reaction equation

HRID 654060 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14](=[O:31])[CH:15]([N:26]1[CH2:29][CH2:28][C:27]1=[O:30])[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH:14]([OH:31])[CH:15]([N:26]1[CH2:29][CH2:28][C:27]1=[O:30])[C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19888202HCID 19888202, compound

Product 1

HCID 14037152HCID 14037152, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 5-benzyloxycarbonylamino-3-oxo-2-(2-oxoazetidin-1-yl)valerate (6.9 mg, 16 μmol) in tetrahydrofuran (1.5 ml) was treated with sodium borohydride (2.2 mg, 58 μmol). After one hour the reaction mixture was analysed by high pressure liquid chromatography using similar conditions to those described in Example 10. The reaction mixture contained the fast moving diastereoisomer of the title compound and slow moving diastereoisomer of the title compound in the ratio 55:45 respectively together with unreacted starting material.

Sources & evidence

ORD record
ord-33cfef25752b4a80973474df5ca65b72
Source dataset
uspto-grants-1992_07
Patent number
US05130241

Reaction notes

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