Acetic Acid → N-Benzyloxycarbonyl-2-amino-2-[4-propoxybenzyl]-ethanol

HRID 1418791Notes

Reaction equation

HRID 1418791 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=1)[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][C:20]([O:23][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=1)[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 22940772N-benzyloxycarbonyl-3-[4-propoxyphenyl]-alanine-methyl ester

Product 1

HCID 67688130N-Benzyloxycarbonyl-2-amino-2-[4-propoxybenzyl]-ethanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

4.15 g (11.2 mmol) of N-benzyloxycarbonyl-3-[4-propoxyphenyl]-alanine-methyl ester is dissolved in 20 ml of tert-butyl methyl ether and mixed with 0.17 g (4.5 mmol) of sodium borohydride. At 0° C., 6 ml of methanol is added and it is stirred for three hours under argon at a temperature below 5° C. Then, 0.8 ml of acetic acid, dissolved in 3 ml of tetrahydrofuran, is added, mixed with 3 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 (eluent: ethyl acetate/hexane).

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 (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-618e053887574cc6b247533a9ccc844b
Source dataset
uspto-grants-1999_03
Patent number
US05885548

Reaction notes

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