Phenylalanine ethyl ester → (S)-2-((S)-1-(3,5-dichlorophenylsulfonyl)pyrrolidine-2-carboxamido)-3-phenylpropanoic acid

HRID 279721Notes

Reaction equation

HRID 279721 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:19][CH2:18][CH2:17][C@H:13]2[C:14]([OH:16])=O)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O:22][C:23](=[O:33])[C@H:24]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH2:25])C>>[Cl:8][C:6]1[CH:5]=[C:4]([S:9]([N:12]2[CH2:19][CH2:18][CH2:17][C@H:13]2[C:14]([NH:25][C@H:24]([C:23]([OH:33])=[O:22])[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:16])(=[O:10])=[O:11])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

3

Reactant 2

HCID 76506Phenylalanine ethyl esterHCID 6559079(2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylic Acid

Product 1

HCID 9847562(S)-2-((S)-1-(3,5-dichlorophenylsulfonyl)pyrrolidine-2-carboxamido)-3-phenylpropanoic acidYield 45%

Procedure

3,5-Dichlorophenyl-sulfonyl-L-proline was coupled to L-phenylalanine ethyl ester using the procedure described in Method 3 to give the ethyl ester of the title compound (348 mg, 45%).

Sources & evidence

ORD record
ord-2fee3a4137b04e20b1c112700263d775
Source dataset
uspto-grants-2002_03
Patent number
US06362341B1

Reaction notes

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