Benzhydrylamine → methyl 3-[N-(diphenylmethyl) aminosulfonyl]-2(R)-methylpropionate

HRID 8835

反応式

HRID 8835 の反応式
[NH2:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[S:23]([CH2:26][C@H:27]([CH3:32])[C:28]([O:30][CH3:31])=[O:29])(=[O:25])=[O:24]>C(Cl)Cl>[C:9]1([CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[NH:1][S:23]([CH2:26][C@H:27]([CH3:32])[C:28]([O:30][CH3:31])=[O:29])(=[O:25])=[O:24])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 7036BenzhydrylamineHCID 8471TriethylamineHCID 18738451methyl 3-chlorosulfonyl-2(R)-methylpropionate

生成物 1

HCID 18738453methyl 3-[N-(diphenylmethyl) aminosulfonyl]-2(R)-methylpropionate収率 66.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A 100 mL round bottom flask equipped with magnetic stir bar was charged with 1 g aminodiphenylmethane, 2 mL triethylamine in 20 mL CH2Cl2. The reaction was cooled to 0° C. and 1 g of methyl 3-chlorosulfonyl-2(R)-methylpropionate was slowly added. The reaction was stirred 1 hour then concentrated in vacuo. The residue was partioned between ethyl acetate and water. The organic phase was washed with brine, dried, and concentrated in vacuo. Trituration from Et2O/hexanes gave 1.15 g of methyl 3-[N-(diphenylmethyl) aminosulfonyl]-2(R)-methylpropionate as a white solid. HRMS (M+Li): calcd. 354.1351, obs 354.1569.

後処理

  1. customA 100 mL round bottom flask equipped with magnetic stir bar
  2. concentrationthen concentrated in vacuo
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-defc4ba15708436b96ff3719a741c0e0
出典データセット
uspto-grants-2006_08
特許番号
US07091219B2

関連ノート

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