Dimethyl Sulfoxide → tert-Butyl [(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]methylcarbamate

HRID 2221071ノート

反応式

HRID 2221071 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16](=[O:32])[N:17]([CH2:19][C@H:20]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=1)[CH2:21][CH2:22][OH:23])[CH3:18])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16](=[O:32])[N:17]([CH2:19][C@H:20]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=1)[CH2:21][CH:22]=[O:23])[CH3:18])([CH3:14])([CH3:12])[CH3:13]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 53843662(S)-[2-(3,4-Dichloro-phenyl)-4-hydroxy-butyl]-methyl-carbamic acid tert-butyl ester

生成物 1

HCID 15433413tert-Butyl [(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]methylcarbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒4 回

反応条件

温度
0 °C

実験手順

To a solution of oxalyl chloride (2.84 mL) in dichloromethane (70 mL) at −78° C. was added dimethylsulfoxide (4.6 mL) in dichloromethane (35 mL). This mixture was stirred for about 7 minutes at −78° C. before (S)-[2-(3,4-dichloro-phenyl)-4-hydroxy-butyl]-methyl-carbamic acid tert-butyl ester (9.1 g) was added as a solution in dichloromethane (25 mL). This mixture was stirred at −78° C. for 30 minutes before triethylamine (18.1 mL) was added neat. The mixture was then stirred for 30 minutes at −78° C., 45 minutes at 0° C., then warmed to ambient temperature. The solution was diluted with dichloromethane, washed with dilute hydrochloric acid, aqueous sodium bicarbonate, dried and evaporated. MS: m/z=346(M+1). The product was used with no further purification.

後処理

  1. additionwas added neat
  2. temperaturewarmed to ambient temperature
  3. washwashed with dilute hydrochloric acid, aqueous sodium bicarbonate
  4. customdried
  5. customevaporated
  6. customThe product was used with no further purification

出典と根拠

ORDレコード
ord-1a365d74ee794d77a0b9f307a5a5f645
出典データセット
uspto-grants-2008_05
特許番号
US07368461B2

反応ノート

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