Lithium borohydride → HCID 178447299, compound

HRID 1609194Notes

Reaction equation

HRID 1609194 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH:30]([CH3:32])[CH3:31])[N:5]([C:24](=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[NH:23][N:22]=[N:21][N:20]=2)=[CH:9][CH:8]=1.[BH4-].[Li+]>C1COCC1>[OH:2][CH2:3][C@@H:4]([N:5]([C:24](=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[NH:23][N:22]=[N:21][N:20]=2)=[CH:11][CH:12]=1)[CH:30]([CH3:32])[CH3:31]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 178447304HCID 178447304, compound

Product 1

HCID 178447299HCID 178447299, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.8 g of N-valeryl-N-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-(L)-valine methyl ester is dissolved in 30 ml of THF, treated at 5° C. with 83 mg of lithium borohydride and stirred at room temperature for 24 h. The reaction mixture is then concentrated, treated with water and adjusted to pH 2 with hydrochloric acid, a white precipitate forming. The mixture is extracted with ethyl acetate, washed with water and brine, dried and finally separated by means of flash chromatography (CH2Cl2 -MeOH 5:1). FAB-MS: m/e=422 (M+H)+.

Workup

  1. concentrationThe reaction mixture is then concentrated
  2. additiontreated with water
  3. customa white precipitate forming
  4. extractionThe mixture is extracted with ethyl acetate
  5. washwashed with water and brine
  6. customdried
  7. customfinally separated by means of flash chromatography (CH2Cl2 -MeOH 5:1)

Sources & evidence

ORD record
ord-5ab661b10dc244f09f1445c57d533084
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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