Triethylamine → Boc-L-phenylalanine methyl ester

HRID 1600389Notes

Reaction equation

HRID 1600389 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:20](N(CC)CC)C.ClCOC=O>ClCCl.CN(C)C1C=CN=CC=1>[CH3:20][O:18][C:17](=[O:19])[C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 17803410Chloromethyl formate

Product 1

HCID 9882138Boc-L-phenylalanine methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8.8 g(0.0344 mol) of N-t-butoxycarbonylphenylalanine in 50ml of dichloromethane were successively added 5.25 ml of triethylamine solution, and 3 ml of chloromethylformate at 0° C. 50 mg of 4-dimethylaminopyridine was added to catalyze the reaction. After the reaction was completed the reaction mixture was extracted with dichloromethane and distilled under a reduced pressure to give the title compound quantitatively.

Workup

  1. customat 0° C
  2. customthe reaction
  3. extractionwas extracted with dichloromethane
  4. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-416bb0e6f35a49029d3214ec95ac3944
Source dataset
uspto-grants-1998_04
Patent number
US05744621

Reaction notes

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