Acetic Acid → HCID 67657124, compound

HRID 1459120Notes

Reaction equation

HRID 1459120 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH2:24][CH2:25][CH2:26][CH3:27])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[BH4-].[Na+].CO.C(O)(=O)C>COC(C)(C)C.O1CCCC1.O>[CH2:9]([O:8][C:6]([NH:5][CH:4]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:3][OH:2])=[O:7])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 22940767HCID 22940767, compound

Product 1

HCID 67657124HCID 67657124, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

3.9 g (11 mmol) of N-benzyloxycarbonyl-3-[2-butoxyphenyl]-alanine-methyl ester (Example a) is dissolved in 30 ml of tert-butyl methyl ether and mixed with 0.55 g (15 mmol) of sodium borohydride. At 3° C., 8 ml of methanol is added, and it is stirred for five hours at constant temperature. Then, 0.8 ml of acetic acid, dissolved in 3 ml of tetrahydrofuran, is added, mixed with 5 ml of water and stirred for ten minutes at room temperature. The organic phase is separated, washed with water and dried on sodium sulfate. The drying agent is suctioned off, the filtrate is concentrated by evaporation and the residue is chromatographed for purification on silica gel.

Workup

  1. additionis added
  2. stirringstirred for ten minutes at room temperature
  3. customThe organic phase is separated
  4. washwashed with water
  5. customdried on sodium sulfate
  6. concentrationthe filtrate is concentrated by evaporation
  7. customthe residue is chromatographed for purification on silica gel

Sources & evidence

ORD record
ord-81cf4929064c49ab8781c4dc93e8f2c6
Source dataset
uspto-grants-1998_12
Patent number
US05853699

Reaction notes

Loading…