Triethylamine → HCID 86649015, compound

HRID 1367455Notes

Reaction equation

HRID 1367455 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C@H:9]([OH:11])[CH2:8][C@H:7]1[C:12]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[O:13])=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C@H:9]([O:11][S:28]([CH3:27])(=[O:30])=[O:29])[CH2:8][C@H:7]1[C:12]([N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)=[O:13])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66918551HCID 66918551, compound

Product 1

HCID 86649015HCID 86649015, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,2R,4R)-4-hydroxy-2-(morpholine-4-carbonyl)-cyclopentanecarboxylic acid ethyl ester (1.0 mmol) in dichloromethane (5 ml) was added at 5° C. triethylamine (2.2 mmol) and methanesulfonyl chloride (2.2 mmol) and stirring was continued for 1 h. The mixture was partitioned between 1 N aqueous HCl and ethyl acetate, the organic layer was dried, evaporated and chromatographed on silica using ethyl acetate to give (1R,2R,4R)-4-methanesulfonyloxy-2-(morpholine-4-carbonyl)-cyclopentanecarboxylic acid ethyl ester as a colorless oil. MS: 350.4 (M+H)+.

Workup

  1. customThe mixture was partitioned between 1 N aqueous HCl and ethyl acetate
  2. customthe organic layer was dried
  3. customevaporated
  4. customchromatographed on silica

Sources & evidence

ORD record
ord-513d0b92e39c420f8e3229ced942b0c6
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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