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

HRID 220777

반응식

HRID 220777 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e70ace56b00e42cb9b06c565f7e98394
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

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