Sodium borohydride → HCID 14037152, compound

HRID 2291359Notes

Reaction equation

HRID 2291359 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-8fff359b10f24143a48e8ea67107ba92
Source dataset
uspto-grants-1989_01
Patent number
US04795809

Reaction notes

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