Dichloromethane → 4-(7-Methoxy-benzo[1,3]dioxol-5-yl)-1,1-dioxo-2-o-tolyl-1,2-dihydro-1lambda6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester

HRID 1265334

반응식

HRID 1265334 반응식
[CH3:1][O:2][C:3](=[O:35])[CH2:4][N:5]([S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([C:24]1[CH:32]=[C:31]([O:33][CH3:34])[C:27]2[O:28][CH2:29][O:30][C:26]=2[CH:25]=1)=O)(=[O:15])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12].ClCCl.C(N(CC)CC)C.P([O-])([O-])([O-])=O.[NH4+].[NH4+].[NH4+]>ClC1CC(C(C)C)CCC1(Cl)C>[CH3:1][O:2][C:3]([C:4]1[N:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH3:12])[S:13](=[O:14])(=[O:15])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]=1[C:24]1[CH:32]=[C:31]([O:33][CH3:34])[C:27]2[O:28][CH2:29][O:30][C:26]=2[CH:25]=1)=[O:35]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 159282Ammonium phosphate, tribasicHCID 22965596{[2-(7-Methoxy-benzo[1,3]dioxole-5-carbonyl)-benzenesulfonyl]-o-tolyl-amino}-acetic acid methyl ester

생성물 1

HCID 155128974-(7-Methoxy-benzo[1,3]dioxol-5-yl)-1,1-dioxo-2-o-tolyl-1,2-dihydro-1lambda6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 21946423Dichloromenthane용매

반응 조건

온도
-60 °C

실험 절차

To a dry 100-mL flask was added {[2-(7-methoxy-benzo[1,3]dioxole-5-carbonyl)-benzenesulfonyl]-o-tolyl-amino}-acetic acid methyl ester (2.0 g, 4.2 mmol), dry 4 angstrom molecular sieves (8 g), and Ti(TfO)2Cl2 (0.56 g, 0.48 mmol). The flask was cooled to −60° C. and dichloromethane (45 mL) was added. A solution of triethylamine (1.35 g, 9.73 mmol) in dichloromenthan (18 mL) was added. The mixture was warmed to 5° C. over 2 hours, followed by refrigeration at 0° C. for 18 hours. The mixture was poured in to 50-mL ammonium phosphate buffer solution (pH 7), stirred 20 minutes, and filtered. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo to an oil. The oil was chromatographed on 150 g silica gel eluted with a mixture of ethyl acetate and hexane (40:60). The appropriate fractions were evaporated in vacuo, and the residue was evaporated to a foam, 1.02 g, 53%. NMR spectra and elemental analysis were consistent with the structure.

후처리

  1. temperatureThe mixture was warmed to 5° C. over 2 hours
  2. filtrationfiltered
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to an oil
  7. customThe oil was chromatographed on 150 g silica gel
  8. washeluted with a mixture of ethyl acetate and hexane (40:60)
  9. customThe appropriate fractions were evaporated in vacuo
  10. customthe residue was evaporated to a foam, 1.02 g, 53%

출처 및 근거

ORD 기록
ord-46d08d94478940ee9d2e9de4202cafa0
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06545150B2

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