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Benzenesulfonamide → N-[4-[6-(Cyclopentyloxycarbonyl)amino-2,3-dihydrobenz-1,4-oxazin-4ylmethyl]-3-methoxybenzoyl]benzenesulphonamide

HRID 1723213
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HRID 1723213 반응식
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:11]1([O:16][C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]3[O:28][CH2:27][CH2:26][N:25]([CH2:29][C:30]4[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][C:31]=4[O:39][CH3:40])[C:24]=3[CH:41]=2)=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH:11]1([O:16][C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]3[O:28][CH2:27][CH2:26][N:25]([CH2:29][C:30]4[CH:38]=[CH:37][C:33]([C:34]([NH:10][S:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)(=[O:9])=[O:8])=[O:35])=[CH:32][C:31]=4[O:39][CH3:40])[C:24]=3[CH:41]=2)=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1
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참가 물질

6

반응물 3

HCID 7370BenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 147631294-[6-(Cyclopentyloxycarbonyl)amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl]-3-methoxybenzoic acid

생성물 1

HCID 14763130N-[4-[6-(Cyclopentyloxycarbonyl)amino-2,3-dihydrobenz-1,4-oxazin-4ylmethyl]-3-methoxybenzoyl]benzenesulphonamide수율 54%

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매2회

실험 절차

Benzenesulphonamide (0.037 g.) was added to a stirred solution of 4-[6-(cyclopentyloxycarbonyl)amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl]-3-methoxybenzoic acid (0.1 g.), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.046 g.) and 4-(dimethylamino)pyridine (0.029 g.) in dichloromethane (5 ml.), under an atmosphere of nitrogen. The mixture was stirred for 21 hours and then diluted with dichloromethane. This mixture was washed successively with 1M hydrochloric acid (2×10 ml.), 5% w/v sodium bicarbonate solution (2×10 ml.), and saturated brine (20 ml.). It was then dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel (3 cm. diameter column) eluting with 1:1 v/v ethyl acetate:hexane. The solid obtained was recrystallized crystallized from ethyl acetate to give the title compound as a white powder (0.071 g., 54%), m.p. 186°-187° C.

후처리

  1. washThis mixture was washed successively with 1M hydrochloric acid (2×10 ml.), 5%
  2. dry with materialIt was then dried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by flash chromatography on silica gel (3 cm. diameter column)
  5. washeluting with 1:1 v/v ethyl acetate
  6. customThe solid obtained
  7. customwas recrystallized
  8. customcrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-39120f12ecf249658922c10f0f2e908e
출처 데이터셋
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04859692

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