Chloride → HCID 68616792, compound

HRID 1158401Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:14][CH:15]2[CH2:17][CH2:16]2)[C@H:10]([CH2:18][N:19]([C:23](=[O:37])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH3:36])[CH:25]=2)[CH:20]([CH3:22])[CH3:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].C(N([CH2:44][CH3:45])CC)C>>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@@H:10]([CH2:18][N:19]([C:23](=[O:37])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH3:36])[CH:25]=2)[CH:20]([CH3:22])[CH3:21])[C@H:11]([CH2:13][N:14]([CH:15]2[CH2:16][CH2:17]2)[C:1](=[O:5])[CH2:2][C:45]2[CH:44]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:12]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 3

HCID 312Chloride

HCID 8471Triethylamine

HCID 68616132HCID 68616132, compound

Product 1

HCID 68616792HCID 68616792, compound

Procedure

From (3R,4R)-3-({[4-methyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-4-cyclopropylaminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.3 g, 0.579 mmol), phenylacethyl chloride (0.092 mL, 0.695 mmol) and triethylamine (0.12 mL, 0.869 mmol) and purification by flash chromatography (c-hexane/AcOEt 1:1 to 0:1) to give the title compound as colorless oil. TLC, Rf (AcOEt/c-hexane 4:1)=0.15. MS (LC-MS): 610.3 [M+H]+; (LC-MS Waters Symmetry C18, 2.1×30 mm, 20-100% CH3CN/5 min): 4.63 min.

Sources & evidence

ORD record: ord-b3aa452253fc4eba8ae4e6a176b3ceaf
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807709B2

Reaction notes

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