1-Hydroxy-2-naphthoic acid → (2S,4S)-1-(3,3-Dimethyl-butyl)-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester

HRID 1477542Notes

Reaction equation

HRID 1477542 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH2:10])[CH2:7][N:6]1[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:4].[OH:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[C:28](O)=[O:29]>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:10][C:28]([C:19]2[CH:20]=[CH:21][C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]=2[OH:17])=[O:29])[CH2:7][N:6]1[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:4]

Participants

3

Reactant 2

HCID 68441-Hydroxy-2-naphthoic acidHCID 89776135(2S,4S)-4-Amino-1-(3,3-dimethyl-butyl)-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 71715909(2S,4S)-1-(3,3-Dimethyl-butyl)-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester

Procedure

(2S,4S)-1-(3,3-Dimethyl-butyl)-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester was prepared from (2S,4S)-4-amino-1-(3,3-dimethyl-butyl)-pyrrolidine-2-carboxylic acid methyl ester and 1-hydroxy-naphthalene-2-carboxylic acid in an analogous manner to example 1. MS calcd. for C23H31N2O4 [(M+H)+] 399.0, obsd. 399.0.

Sources & evidence

ORD record
ord-254e38af9e89430cb4e88938e1b041b3
Source dataset
uspto-grants-2016_08
Patent number
US09403805B2

Reaction notes

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