Acetonitrile → Benzyl-carbamic acid (3S*,4S*)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidin-3-ylmethyl ester

HRID 1158334Notes

Reaction equation

HRID 1158334 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]O)[CH2:9]1)=O)(C)(C)C.[CH2:36]([N:43]=[C:44]=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.CC#N.[OH2:49].CC#N>O>[CH:31]([N:14]([CH2:13][C@@H:11]1[CH2:12][NH:8][CH2:9][C@H:10]1[CH2:34][O:45][C:44](=[O:49])[NH:43][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:15](=[O:30])[C:16]1[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]=1)([CH3:32])[CH3:33]

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 76639Benzyl isocyanateHCID 18373917Acetonitrile--water (1/1)HCID 59512299(3S,4R)-3-Hydroxymethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 11851631Benzyl-carbamic acid (3S*,4S*)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidin-3-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound is prepared analogously as described in Example 3 from (3S*,4R*)-3-hydroxymethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester and benzylisocyanate. MS (LC-MS): 528.3 [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): 4.52 min.

Workup

  1. custom4.52 min.

Sources & evidence

ORD record
ord-6318f40da716468bb9ab30f826bd0a55
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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