1,2-Dichloroethane → 2-Trityloxycarbamoyl-benzo[b]thiophene-5-carboxylic acid methyl ester

HRID 545474ノート

反応式

HRID 545474 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[S:9][C:10]([C:12]([OH:14])=O)=[CH:11][C:7]=2[CH:6]=1)=[O:4].[C:17]([O:36][NH2:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[S:9][C:10]([C:12](=[O:14])[NH:37][O:36][C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:11][C:7]=2[CH:6]=1)=[O:4]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 3015602O-(triphenylmethyl)hydroxylamineHCID 595564095-(Methoxycarbonyl)benzo[b]thiophene-2-carboxylic acid

生成物 1

HCID 866150442-Trityloxycarbamoyl-benzo[b]thiophene-5-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of benzo[b]thiophene-2,5-dicarboxylic acid 5-methyl ester (2.592 g, 10.97 mmol), O-trityl -hydroxylamine (3.020 g, 10.97 mmol), EDC (3.150 g, 16.48 mmol), HOBt (1.482 g, 10.97 mmol) and DIEA (4.80 mL, 27.6 mmol) in anhydrous THF (100 mL) was allowed to stir at rt for one week and then concentrated. To the residue was added MeOH (10 mL) and water (100 mL). The syrup obtained was washed with water (10 mL) and triturated with water (90 mL) to give 2-trityloxycarbamoyl-benzo[b]thiophene-5-carboxylic acid methyl ester as a pale solid. MS (EI): cal'd 243.1 (M-benzothiophene moiety+H+), exp 243.2 (M-benzothiophene moiety+H+).

後処理

  1. concentrationconcentrated
  2. additionTo the residue was added MeOH (10 mL) and water (100 mL)
  3. customThe syrup obtained
  4. washwas washed with water (10 mL)
  5. customtriturated with water (90 mL)

出典と根拠

ORDレコード
ord-ca428f3e6b474114af183f0b7910d400
出典データセット
uspto-grants-2011_05
特許番号
US07935724B2

反応ノート

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