Methylamine → HCID 66877038, compound

HRID 503952Notes

Reaction equation

HRID 503952 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)(=[O:21])=[O:20])=[CH:15][C:14]=2[O:29][CH2:30][C:31](OC)=[O:32])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:35][NH2:36]>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)(=[O:20])=[O:21])=[CH:15][C:14]=2[O:29][CH2:30][C:31](=[O:32])[NH:36][CH3:35])[CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 66877432HCID 66877432, compound

Product 1

HCID 66877038HCID 66877038, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 3-[4-(3-fluoro-benzenesulfonyl)-2-methoxycarbonylmethoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (120 mg, prepared as described in Example 13) and methylamine (2M in THF, 1.2 mL) was heated at 90° C. in a sealed tube for 16 hours. The reaction mixture was cooled and concentrated under reduced pressure, and the crude residue was purified via flash chromatography (hexane/EtOAc, 3/7) to give 109 mg of 3-[4-(3-fluoro-benzenesulfonyl)-2-methylcarbamoylmethoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customthe crude residue was purified via flash chromatography (hexane/EtOAc, 3/7)

Sources & evidence

ORD record
ord-f6bccb9b459543e7b031ca59997a14ef
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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