(3R*,4R*)-3-(1-cyclopropyl-3-methyl-3-phenyl-ureidomethyl)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester → N-[(3S*,4S*)-4-(1-Cyclopropyl-3-methyl-3-phenyl-ureidomethyl)-pyrrolidin-3-ylmethyl]-N-isopropyl-4-methoxy-3-(3-methoxy-propoxy)-benzamide

HRID 1158434Notes

Reaction equation

HRID 1158434 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:31]([CH3:33])[CH3:32])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:10]([CH2:34][N:35]([CH:46]2[CH2:48][CH2:47]2)[C:36]([N:38]([CH3:45])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:37])[CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[CH:46]1([N:35]([CH2:34][C@@H:10]2[CH2:9][NH:8][CH2:12][C@H:11]2[CH2:13][N:14]([CH:31]([CH3:33])[CH3:32])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C:36]([N:38]([CH3:45])[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:37])[CH2:48][CH2:47]1

Participants

3

Reactant 1

HCID 68615828(3R*,4R*)-3-(1-cyclopropyl-3-methyl-3-phenyl-ureidomethyl)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59512282N-[(3S*,4S*)-4-(1-Cyclopropyl-3-methyl-3-phenyl-ureidomethyl)-pyrrolidin-3-ylmethyl]-N-isopropyl-4-methoxy-3-(3-methoxy-propoxy)-benzamide

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of (3R*,4R*)-3-(1-cyclopropyl-3-methyl-3-phenyl-ureidomethyl)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (195 mg, 0.29 mmol) in 4N HCl/dioxane (8 mL) is stirred at RT until the reaction is complete. Lyophilization affords the title compound as a colorless foam. MS (LC-MS): 567.1 [M+H]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 ml/min): 4.57 min.

Sources & evidence

ORD record
ord-3c37ab3a8a0246ebac7d8a5c6e1ea5ac
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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