Water → 2-(2-{4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)-phenoxy]-phenyl}-1-methoxycarbonylethylcarbamoyl)-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

HRID 7349

反応式

HRID 7349 の反応式
Cl.[NH2:2][CH:3]([C:26]([O:28][CH3:29])=[O:27])[CH2:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:23]=[CH:22][C:13]([CH:14]=[C:15]3[S:19][C:18](=[O:20])[NH:17][C:16]3=[O:21])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1.[C:30]([N:37]1[CH2:41][CH2:40][CH2:39][CH:38]1[C:42](O)=[O:43])([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].C1(N=C=NC2CCCCC2)CCCCC1.O>CN(C)C=O.C(OCC)(=O)C>[C:33]([O:32][C:30]([N:37]1[CH2:41][CH2:40][CH2:39][CH:38]1[C:42](=[O:43])[NH:2][CH:3]([C:26]([O:28][CH3:29])=[O:27])[CH2:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:23]=[CH:22][C:13]([CH:14]=[C:15]3[S:19][C:18](=[O:20])[NH:17][C:16]3=[O:21])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)=[O:31])([CH3:36])([CH3:35])[CH3:34]

参加物

7

反応物 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 2684721-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 730387885[4-(4-(2-Amino-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione hydrochloride

生成物 1

HCID 865974412-(2-{4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)-phenoxy]-phenyl}-1-methoxycarbonylethylcarbamoyl)-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester収率 32.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 5[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione hydrochloride (2.5 g, 5.76 mmol) and N-Boc-pyrolidin-2-carboxylic acid (1.238 g, 5.76 mmol) in dimethyl formamide (25 ml) was stirred for 60 minutes at 0° C. N,N′-Dicyclohexylcarbodiimide (1.423 g, 6.91 mmol) was added to it and stirring was continued for 10 h at ambient temperature. Water (200 ml) was added to the reaction mixture and stirred for 15 minutes. Ethyl acetate (200 ml) was added to the reaction mixture and stirring continued for another 15 minutes. The organic layer was separated, washed with water (75 ml), dried over anhydrous sodium sulphate and concentrated to afford the crude product, which was purified by column chromatography to furnish the required product (1.1 g, yield 32.4%).

後処理

  1. stirringstirred for 15 minutes
  2. stirringstirring
  3. waitcontinued for another 15 minutes
  4. customThe organic layer was separated
  5. washwashed with water (75 ml)
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated
  8. customto afford the crude product, which
  9. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-63d709e139114d61af6aab85262e9c8f
出典データセット
uspto-grants-2006_08
特許番号
US07087576B2

関連ノート

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