Oxalyl chloride → HCID 22719746, compound

HRID 1582072Notes

Reaction equation

HRID 1582072 reaction equation
C(Cl)(=O)C([Cl:4])=O.[CH2:7]([O:14][C:15]([CH:17]([CH2:27][CH2:28][CH3:29])[CH2:18][C:19]1([C:24](O)=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>ClCCl>[Cl:4][C:24]([C:19]1([CH2:18][CH:17]([CH2:27][CH2:28][CH3:29])[C:15]([O:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:16])[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:25]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 22719744HCID 22719744, compound

Product 1

HCID 22719746HCID 22719746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (1.15 ml, 13.2 mmol) was added to an ice-cooled solution of 1-{2-[(benzyloxy)carbonyl]pentyl}cyclopentanecarboxylic acid (EP 274234) (2.0 g, 6.3 mmol) in dry dichloromethane (20 ml), and the solution stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue azetroed with dichloromethane (3×), to give the title compound as a golden oil, 2.1 g; 1H NMR (CDCl3, 300 MHz) δ: 0.88 (t, 3H), 1.28 (m, 2H), 1.43 (m, 2H), 1.63 (m, 6H), 2.00 (m, 1H), 2.08-2.35 (m, 3H), 2.44 (m, 1H), 5.15 (s, 2H), 7.28 (m, 5H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-13f6d18069d94c9d88fa1b959ef60687
Source dataset
uspto-grants-2004_05
Patent number
US06734186B1

Reaction notes

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