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

HRID 528585ノート

反応式

HRID 528585 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-ff1778cceecc4bdf837a45f811432570
出典データセット
uspto-grants-2016_05
特許番号
US09346798B2

反応ノート

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