Phenylacetyl chloride → HCID 68616931, compound

HRID 1158392Notes

Reaction equation

HRID 1158392 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:14][CH3:15])[C@H:10]([CH2:16][N:17]([C:21](=[O:36])[C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[C:24]([O:30][CH2:31][CH2:32][CH2:33][O:34][CH3:35])[CH:23]=2)[CH:18]([CH3:20])[CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:37]1([CH2:43][C:44](Cl)=[O:45])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH3:15])[C:44](=[O:45])[CH2:43][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:10]([CH2:16][N:17]([C:21](=[O:36])[C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[C:24]([O:30][CH2:31][CH2:32][CH2:33][O:34][CH3:35])[CH:23]=2)[CH:18]([CH3:19])[CH3:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 68617139HCID 68617139, compound

Product 1

HCID 68616931HCID 68616931, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

From (3R,4R)-3-({[4-ethyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-4-methylaminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.7 g, 1.38 mmol), phenylacetyl chloride (0.22 mL, 1.66 mmol) and triethylamine (0.21 mL, 2.1 mmol) in CH2Cl2 (40 mL) and purification by flash chromatography on silica gel (c-hexane/AcOEt 1:1 to 0:1) to give the title compound as colorless oil. TLC, Rf (AcOEt)=0.30. MS (LC-MS): 624.0 [M+H]+; tR (Waters Symmetry C18 column, 20-100% CH3CN/H2O/5 min, CH3CN and H2O containing 0.1% TFA, flow: 0.6 mL/min): 4.41 min.

Sources & evidence

ORD record
ord-1e355e053d5d4111b73601b002cc69bd
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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