Triethylamine → Methyl 3-hydroxy-2-{[4-(trifluoromethyl)phenyl]carbonylamino}propanoate

HRID 1827882ノート

反応式

HRID 1827882 の反応式
Cl.[NH2:2][CH:3]([CH2:8][OH:9])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>ClCCl>[OH:9][CH2:8][CH:3]([NH:2][C:23]([C:22]1[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:28])[F:29])=[CH:27][CH:26]=1)=[O:24])[C:4]([O:6][CH3:7])=[O:5]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 517373Methyl DL-serinate hydrochloride

生成物 1

HCID 22064268Methyl 3-hydroxy-2-{[4-(trifluoromethyl)phenyl]carbonylamino}propanoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Methyl 2-amino-3-hydroxypropanoate hydrochloride (L-serine methyl ester hydrochloride, 1.71 g, 11 mmol) was stirred in dichloromethane (20 ml) at 0° C., and triethylamine (2.79 ml, 20 mmol) added, followed by dropwise addition of 4-trifluoromethylbenzoyl chloride (1.486 ml, 11 mmol). The mixture was stirred at 0° C. for 30 minutes, then partitioned between dichloromethane and water, dried over magnesium sulfate, and filtered. Solvent was removed from the filtrate under reduced pressure, and the residue was purified by column chromatography, to yield methyl 3-hydroxy-2-{[4-(trifluoromethyl)phenyl]carbonylamino}propanoate, a compound of formula (13).

後処理

  1. custompartitioned between dichloromethane and water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customSolvent was removed from the filtrate under reduced pressure
  5. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-f4d9822882704d93be894e380bcf188f
出典データセット
uspto-grants-2006_06
特許番号
US07056924B2

反応ノート

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