Triethylamine → Boc-D-phenylalanine

HRID 2414044Notes

Reaction equation

HRID 2414044 reaction equation
[NH2:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:20]([O:24][C:25](ON=C(C1C=CC=CC=1)C#N)=[O:26])([CH3:23])([CH3:22])[CH3:21]>CC(C)=O.O>[C:20]([O:24][C:25]([NH:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 71567D-PhenylalanineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Product 1

HCID 637610Boc-D-phenylalanine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a suspension of D-phenylalanine (33.0 g, 0.2 mol) in acetone (120 ml) and water (120 ml) was added triethylamine (41.8 ml, 1.5 eq) followed by 2-(t-butoxycarbonyloxyimino)-2-phenylacetonitrile (54.2 g, 1.1 eq). The resulting mixture was stirred overnight and then diluted with water (250 ml). The aqueous fraction was extracted twice with ether and the ether fractions were discarded. The aqueous fraction was acidified with 0.5M citric acid and extracted with ethyl acetate (2×500 ml). The ethyl acetate fractions were combined and washed with water and brine. After drying over anhydrous magnesium sulfate, the solvent was removed to give the title compound as a viscous yellow oil: 52.2 g.

Workup

  1. extractionThe aqueous fraction was extracted twice with ether
  2. extractionextracted with ethyl acetate (2×500 ml)
  3. washwashed with water and brine
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-1f7c175116db43309eab89781bc6e463
Source dataset
uspto-grants-1988_01
Patent number
US04720585

Reaction notes

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