methoxymethyl (4R)-3-benzoyl-1,1-dioxothiazolidine-4-carboxylate → (4R)-3-Benzoyl-1,1-dioxothiazolidine-4-carboxylic acid

HRID 1200144ノート

反応式

HRID 1200144 の反応式
[C:1]([N:9]1[C@H:13]([C:14]([O:16]COC)=[O:15])[CH2:12][S:11](=[O:21])(=[O:20])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.O>[C:1]([N:9]1[C@H:13]([C:14]([OH:16])=[O:15])[CH2:12][S:11](=[O:20])(=[O:21])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 1

HCID 13986806methoxymethyl (4R)-3-benzoyl-1,1-dioxothiazolidine-4-carboxylate

生成物 1

HCID 13986804(4R)-3-Benzoyl-1,1-dioxothiazolidine-4-carboxylic acid収率 80.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

31.3 g of methoxymethyl (4R)-3-benzoyl-1,1-dioxothiazolidine-4-carboxylate (prepared as described in Preparation 11) were dissolved in 200 ml of a 1:1 by volume mixture of trifluoroacetic acid and water, and then the mixture was stirred at room temperature for 1 hour. The reaction mixture was then concentrated by evaporation under reduced pressure to leave crystals. These crystals were washed with 150 ml of water and then recrystallized from ethyl acetate to give 21.6 g (80.3%) of the title compound in the form of colorless needles melting at 175°-176° C.

後処理

  1. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  2. customto leave crystals
  3. washThese crystals were washed with 150 ml of water
  4. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-559435ee05324a07adffa8734ea68131
出典データセット
uspto-grants-1990_02
特許番号
US04904680

反応ノート

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