Trifluoroacetic acid → 4-nitrophenyl 7-(N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-carboxylate

HRID 528585

반응식

HRID 528585 반응식
COC1C=CC(C[N:8]([C:34]2[S:35][CH:36]=[CH:37][N:38]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[N:20]([C:21]([O:23][C:24]4[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=4)=[O:22])[CH2:19][CH2:18][O:17][C:16]=3[CH:33]=2)(=[O:11])=[O:10])=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[S:35]1[CH:36]=[CH:37][N:38]=[C:34]1[NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]2[N:20]([C:21]([O:23][C:24]3[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=3)=[O:22])[CH2:19][CH2:18][O:17][C:16]=2[CH:33]=1)(=[O:11])=[O:10]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 897616924-nitrophenyl 7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-carboxylate

생성물 1

HCID 897619374-nitrophenyl 7-(N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-carboxylate수율 91%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-nitrophenyl 7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-carboxylate (0.050 g, 0.086 mmol) in DCM (0.172 ml) was added trifluoroacetic acid (0.165 ml, 2.146 mmol). The reaction was stirred at RT for 15 minutes until complete deprotection. The reaction was concentrated in vacuo and purified via 500-mg SCX column (product eluted cleanly with methanol wash) to yield, after concentration, 4-nitrophenyl 7-(N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazine-4(3 H)-carboxylate (0.036 g, 0.078 mmol, 91% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.73 (br. s., 1 H) 8.28-8.38 (m, 2 H) 8.06 (d, J=8.71 Hz, 1 H) 7.55-7.64 (m, 2 H) 7.34 (dd, J=8.75, 2.20 Hz, 1 H) 7.22-7.30 (m, 2 H) 6.83 (d, J=4.60 Hz, 1 H) 4.36-4.48 (m, 2 H) 4.02-4.11 (m, 2 H). m/z (ESI) 462.9 (M+H)+.

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified via 500-mg SCX column (product
  3. washeluted cleanly with methanol
  4. washwash)
  5. customto yield

출처 및 근거

ORD 기록
ord-ff1778cceecc4bdf837a45f811432570
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346798B2

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