Acetic Acid → HCID 69972127, compound

HRID 2271007Notes

Reaction equation

HRID 2271007 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11](=O)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][CH2:23][CH2:24][OH:25].CC(O)=O.[BH3-]C#N.[Na+]>CO>[CH2:1]([O:8][CH2:9][C@H:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:11]([NH:22][CH2:23][CH2:24][OH:25])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 700EthanolamineHCID 5003444Sodium cyanoborohydrideHCID 56982192HCID 56982192, compound

Product 1

HCID 69972127HCID 69972127, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of (3S)-4-benzyloxy-3-tert-butoxycarbonylamino-2-butanone (4.3 g) in dry MeOH (20 ml) was added to a solution of 2-aminoethanol (2.0 g) and AcOH (1.8 g) in dry MeOH (20 ml). NaBH3CN (1.4 g) was added and the mixture was stirred at ambient temperature overnight. The mixture was concentrated in vacuo and the residue was partitioned between AcOEt and aqueous NaHCO3 solution. The organic layer was washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution. The organic layer was mixed with 1N HCl (50 ml) and the mixture was stirred vigorously for 1 hour. The organic layer was separated, washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution, dried over MgSO4 and concentrated in vacuo to give 4.1 g of (2R, 3RS)-O-benzyl-2-tert-butoxycarbonylamino-3-(2-hydroxyethylamino)butanol as an oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between AcOEt and aqueous NaHCO3 solution
  3. washThe organic layer was washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
  4. additionThe organic layer was mixed with 1N HCl (50 ml)
  5. stirringthe mixture was stirred vigorously for 1 hour
  6. customThe organic layer was separated
  7. washwashed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a6f09165131441f9627d230631cb5da
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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