Dl-Phenylalanine → 1170-76-9

HRID 894353Notes

Reaction equation

HRID 894353 reaction equation
[C:1]([NH:11][CH2:12][C:13]([OH:15])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:31][CH:32]([C:40]([OH:42])=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1(C)C=CC=CC=1>[C:1]([NH:11][CH2:12][C:13]([NH:31][CH:32]([C:40]([OH:42])=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:15])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

6

Reactant 4

HCID 994Dl-PhenylalanineHCID 79724-MethylmorpholineHCID 14349BenzyloxycarbonylglycineHCID 62365Isobutyl chloroformate

Product 1

HCID 708891170-76-9Yield 70.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4.2 g (0.02 mole) of N-carbobenzoxyglycine and 2.2 g (0.022 mole) of N-methylmorpholine in 50 ml of dry toluene was cooled to -5° and 2.8 g (0.02 mole) of isobutyl chloroformate was added thereto. After 1 hour, a solution of 3.3 g (0.02 mole) of DL-phenylalanine in 20 ml of N-sodium hydroxide was added and the mixture was stirred vigorously overnight. The aqueous phase was isolated, extracted with ether and acidified with 4 N Hydrochloric acid to precipitate the product as a colorless oil which crystallized upon cooling. Recrystallization from ethanol-water yielded 5 g (70%) of N-carbobenzoxyglycyl-DL-phenylalanine, mp 158°-160° C., RfA 0.61.

Workup

  1. customThe aqueous phase was isolated
  2. extractionextracted with ether
  3. customto precipitate the product as a colorless oil which
  4. customcrystallized
  5. temperatureupon cooling
  6. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-b11a5a3e9dc842a8b83cc28ce44c2930
Source dataset
uspto-grants-1981_08
Patent number
US04283328

Reaction notes

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