Dicyclohexylamine → (S)-1-[2-(3,3-Dicyclohexyl-ureido)-thiazole-5-sulfonyl]-pyrrolidine-2-carboxylic acid

HRID 731453Notes

Reaction equation

HRID 731453 reaction equation
[CH:1]1([N:7]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[C:8](=[O:23])[NH:9][C:10]2[S:11][C:12]([S:15]([NH:18][CH2:19][C:20]([OH:22])=[O:21])(=[O:17])=[O:16])=[CH:13][N:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:30]1(NC2CCCCC2)[CH2:35]CCC[CH2:31]1.COC([C@@H]1CCCN1S(C1SC(N)=NC=1)(=O)=O)=O>>[CH:24]1([N:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:8](=[O:23])[NH:9][C:10]2[S:11][C:12]([S:15]([N:18]3[CH2:35][CH2:30][CH2:31][C@H:19]3[C:20]([OH:22])=[O:21])(=[O:16])=[O:17])=[CH:13][N:14]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 3

HCID 7582DicyclohexylamineHCID 57688273N-{2-[(Dicyclohexylcarbamoyl)amino]-1,3-thiazole-5-sulfonyl}glycineHCID 86629877(S)-1-(2-aminothiazole-5-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 57688281(S)-1-[2-(3,3-Dicyclohexyl-ureido)-thiazole-5-sulfonyl]-pyrrolidine-2-carboxylic acid

Procedure

Prepared in a similar manner to [2-(3,3-dicyclohexyl-ureido)-thiazole-5-sulfonylamino]-acetic acid via dicyclohexylamine and (S)-1-(2-amino-thiazole-5-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester to give the title compound.

Sources & evidence

ORD record
ord-546559ae712d45f99ae3f1a759b5a2da
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Reaction notes

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