Acetyl chloride → HCID 11724686, compound

HRID 859224Notes

Reaction equation

HRID 859224 reaction equation
Cl.[NH2:2][CH:3]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)=[CH:10][CH:9]=2)[C:5](=[O:23])[CH2:4]1.C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>ClCCl>[F:22][C:18]1[CH:17]=[C:16](/[CH:15]=[CH:14]/[C:11]2[CH:10]=[CH:9][C:8]([N:6]3[C:5](=[O:23])[CH2:4][CH:3]([NH:2][C:31](=[O:33])[CH3:32])[CH2:7]3)=[CH:13][CH:12]=2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68615393HCID 68615393, compound

Product 1

HCID 11724686HCID 11724686, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 61 mg (0.18 mmol) of (RS)-(E)-4-amino-1-{4-[2-(3-fluoro-phenyl)-vinyl]-phenyl}-pyrrolidin-2-one hydrochloride in 2.5 ml of dichloromethane is treated with 45 mg (0.44 mmol) of triethylamine. The mixture is cooled to 0° C. and, thereafter, 20 mg (0.26 mmol) of acetylchloride are added. After 1 hour at 0° C., the mixture is left to warm to RT and is diluted with dichloromethane. After washing with water, the organic layer is dried over magnesium sulfate and evaporated. The crude product is crystallised from ether to yield 49 mg (78% of theory) of (RS)-(E)-N-(1-{4-[2-(3-fluoro-phenyl)-vinyl]-phenyl}-5-oxo-pyrrolidin-3-yl)-acetamide as a light brown solid; MS: m/e=339 (M+H)+.

Workup

  1. waitthe mixture is left
  2. temperatureto warm to RT
  3. washAfter washing with water
  4. dry with materialthe organic layer is dried over magnesium sulfate
  5. customevaporated
  6. customThe crude product is crystallised from ether

Sources & evidence

ORD record
ord-1104ed953e9f4528ac1e4705f8a11fad
Source dataset
uspto-grants-2006_12
Patent number
US07151111B2

Reaction notes

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