Acetic Acid → N-Benzyloxycarbonyl-2-amino-2-[4-(1,4,7-trioxaoctyl)benzyl]-ethanol

HRID 1459107Notes

Reaction equation

HRID 1459107 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][O:26][CH2:27][CH2:28][O:29][CH3:30])=[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][O:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:19][CH:18]=1)[CH2:3][OH:2])=[O:7])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 22940770N-benzyloxycarbonyl-3-[4-(1,4,7-trioxaoctyl)-phenyl]-alanine-methyl ester

Product 1

HCID 67688276N-Benzyloxycarbonyl-2-amino-2-[4-(1,4,7-trioxaoctyl)benzyl]-ethanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

7.35 g (17 mmol) of N-benzyloxycarbonyl-3-[4-(1,4,7-trioxaoctyl)-phenyl]-alanine-methyl ester (Example a) is dissolved in 35 ml of tert-butyl methyl ether and mixed with 0.9 g (23.8 mmol) of sodium borohydride. At 5° C., 10 ml of methanol is added, and it is stirred for four hours under argon at constant temperature. Then, 1.5 ml of acetic acid, dissolved in 5 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-1f4febcc62544566b10ea6bc4dfdc3a0
Source dataset
uspto-grants-1998_12
Patent number
US05853699

Reaction notes

Loading…