Acetic Acid → 1-Tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

HRID 220777

反応式

HRID 220777 の反応式
COC([C:5]1[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[C:8]2[CH:22]=[CH:23][CH:24]=[CH:25][C:7]=2[C:6]=1[OH:26])=O.C(OC(C1CCN(S(C2C=CC(C)=CC=2)(=O)=O)C2C=CC=CC=2C=1O)=O)C.C(O)(=O)C.Cl>C(O)C.O>[C:18]1([CH3:21])[CH:17]=[CH:16][C:15]([S:12]([N:9]2[CH2:10][CH2:11][CH2:5][C:6](=[O:26])[C:7]3[CH:25]=[CH:24][CH:23]=[CH:22][C:8]2=3)(=[O:14])=[O:13])=[CH:20][CH:19]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 54718720ethyl 5-hydroxy-1-tosyl-2,3-dihydro-1H-benzo[b]azepine-4-carboxylateHCID 575553885-hydroxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-benzo[b]azepine-4-carboxylic acid methyl ester

生成物 1

HCID 2668521-Tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one収率 60%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

A mixture of 5-hydroxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-benzo[b]azepine-4-carboxylic acid methyl ester and 5-hydroxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-benzo[b]azepine-4-carboxylic acid ethyl ester from Example E5.3 were heated at reflux in a mixture of ethanol (100 ml), acetic acid (300 ml), concentrated HCl (100 ml) and water (50 ml) for 18 h. The mixture was cooled to room temperature, diluted with water (800 ml) and extracted with chloroform. The combined organic ex-tracts were dried, filtered and reduced in vacuo. The residue was crystallised twice from methanol to yield the title compound (44 g, 60% over two steps).

後処理

  1. temperaturewere heated
  2. extractionextracted with chloroform
  3. customThe combined organic ex-tracts were dried
  4. filtrationfiltered
  5. customThe residue was crystallised twice from methanol

出典と根拠

ORDレコード
ord-e70ace56b00e42cb9b06c565f7e98394
出典データセット
uspto-grants-2012_06
特許番号
US08202858B2

関連ノート

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