Benzyl Bromide → 4-Keto-1-[(phenylmethoxy)carbonyl]-L-proline benzyl ester

HRID 570037

Reaction equation

HRID 570037 reaction equation
[O:1]=[C:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C@H:4]([C:17]([OH:19])=[O:18])[CH2:3]1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:20]([O:18][C:17](=[O:19])[C@@H:4]1[CH2:3][C:2](=[O:1])[CH2:6][N:5]1[C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11076282N-Carbobenzyloxy-4-keto-L-proline

Product 1

HCID 116245254-Keto-1-[(phenylmethoxy)carbonyl]-L-proline benzyl esterYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g (0.02 mmol) of 4-keto-1-[(phenylmethoxy)carbonyl]-L-proline was dissolved in 50 ml dimethylformamide, 2.62 ml (0.022 mmol) of benzyl bromide and 3.59 g (0.026 mmol) of potassium carbonate were added. The reaction mixture was stirred for 1 hour followed by normal extractive work to give the title compound, 3.5 gm (49% yield), m.p. 55°-56° C.

Sources & evidence

ORD record
ord-a1ceb4f81a6a4bf2835b2d542bc418b1
Source dataset
uspto-grants-1988_03
Patent number
US04734508

Linked notes

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