Sodium borohydride → HCID 86739671, compound

HRID 1632177Notes

Reaction equation

HRID 1632177 reaction equation
[C:1]([NH:9][CH:10]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:11](=[O:33])[CH2:12][NH:13][C@H:14]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]([CH2:21][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[C:15]1=[O:32])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>O1CCCC1.O>[C:1]([NH:9][CH:10]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[CH:11]([OH:33])[CH2:12][NH:13][C@H:14]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]([CH2:21][C:22]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:23])[C:15]1=[O:32])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86739670HCID 86739670, compound

Product 1

HCID 86739671HCID 86739671, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-3-[[3-(benzoylamino)-2-oxo-4-phenylbutyl]amino]-hexahydro-2-oxo-1H-azepine-1-acetic acid, phenylmethyl ester (2.5 mmole) in tetrahydrofuran (25 ml.) and water (2.5 ml.) is added sodium borohydride (10.0 mmole) portionwise over a 10 minute period. After the addition is completed, the reaction mixture is stirred for 4 hours, and slowly quenched with concentrated hydrochloric acid. The mixture is diluted with ethyl acetate (50 ml.), washed with water (2×), saturated sodium bicarbonate (2×), and saturated sodium chloride (2×), dried (Na2SO4), and concentrated under reduced pressure to give (S)-3-[[3-(benzoylamino)-2-hydroxy-4-phenylbutyl]amino]hexahydro-2-oxo-1H-azepine-1-acetic acid, phenylmethyl ester.

Workup

  1. additionAfter the addition
  2. customslowly quenched with concentrated hydrochloric acid
  3. additionThe mixture is diluted with ethyl acetate (50 ml.)
  4. washwashed with water (2×), saturated sodium bicarbonate (2×), and saturated sodium chloride (2×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-95beb45c6e2c4669a9e519e15cdad886
Source dataset
uspto-grants-1984_10
Patent number
US04474778

Reaction notes

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