Cyclohexanecarboxaldehyde → Hydroxy-naphthalene-2-carboxylic acid ((3S,5S)-1-cyclohexylmethyl-5-oxazol-2-yl-pyrrolidin-3-yl)-amide

HRID 1477562Notes

Reaction equation

HRID 1477562 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C@H:6]1[NH:10][CH2:9][C@@H:8]([NH:11][C:12]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[OH:24])=[O:13])[CH2:7]1.[CH:25]1([CH:31]=O)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.COC([C@@H]1C[C@H](N=[N+]=[N-])CN1CC1CCCCC1)=O>>[CH:25]1([CH2:31][N:10]2[C@H:6]([C:2]3[O:1][CH:5]=[CH:4][N:3]=3)[CH2:7][C@H:8]([NH:11][C:12]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]=3[OH:24])=[O:13])[CH2:9]2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 3

HCID 16275CyclohexanecarboxaldehydeHCID 897762371-hydroxy-naphthalene-2-carboxylic acid ((3S,5S)-5-oxazol-2-yl-pyrrolidin-3-yl)-amideHCID 117774177(2S,4S)-4-azido-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 71715055Hydroxy-naphthalene-2-carboxylic acid ((3S,5S)-1-cyclohexylmethyl-5-oxazol-2-yl-pyrrolidin-3-yl)-amide

Procedure

Hydroxy-naphthalene-2-carboxylic acid ((3S,5S)-1-cyclohexylmethyl-5-oxazol-2-yl-pyrrolidin-3-yl)-amide was prepared from 1-hydroxy-naphthalene-2-carboxylic acid ((3S,5S)-5-oxazol-2-yl-pyrrolidin-3-yl)-amide and cyclohexanecarbaldehyde in a similar fashion as the synthesis of (2S,4S)-4-azido-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester. MS calcd. for C25H30N3O3[(M+H)+] 420, obsd. 419.8.

Sources & evidence

ORD record
ord-594e505d1e814583b94155c6a25def86
Source dataset
uspto-grants-2016_08
Patent number
US09403805B2

Reaction notes

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