Benzyl chloroformate → Z-L-2-Nal-OH

HRID 742889Notes

Reaction equation

HRID 742889 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C@@H:12]([C:14]([OH:16])=[O:15])[NH2:13].[OH-].[Na+].Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>O>[CH2:23]([O:22][C:20]([NH:13][C@H:12]([C:14]([OH:16])=[O:15])[CH2:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 1859152-Naphthylalanine

Product 1

HCID 7023496Z-L-2-Nal-OH

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

5 g of 3-(2-naphthyl)-L-alanine and 0.93 g of sodium hydroxide in 12 ml of water were cooled to 0° C. and stirred while a solution of 1.4 g of sodium hydroxide in 9 ml of water and 5 ml of benzyl chloroformate were added simultaneously during 10 minutes. Stirring was continued for 2 hours and the mixture was allowed to come to room temperature. The mixture was diluted with water and then extracted with diethyl ether. The aqueous layer was acidified with 4 ml of concentrated hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extracts were back-washed with water. The combined ethyl acetate extracts were dried over sodium sulphate, filtered, evaporated and triturated with petroleum ether (boiling point 40°-60° C.) to give 7.5 g of N-(benzyloxycarbonyl)-3-(2-naphthyl)-L-alanine of melting point 109°-111° C.

Workup

  1. additionwere added simultaneously during 10 minutes
  2. customto come to room temperature
  3. extractionextracted with diethyl ether
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate extracts were back-washed with water
  6. dry with materialThe combined ethyl acetate extracts were dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customtriturated with petroleum ether (boiling point 40°-60° C.)

Sources & evidence

ORD record
ord-c11afd46f85547e0a2f249cb3428bf75
Source dataset
uspto-grants-1996_09
Patent number
US05554756

Reaction notes

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