HCID 86636267, 화합물 → tert-Butyl (3-{[(3-aminobenzyl)sulfonyl]amino}phenyl)carbamate

HRID 541826노트

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HRID 541826 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[CH2:7][S:8]([NH:11][C:12]1[CH:13]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=[CH:16][CH:17]=1)(=[O:10])=[O:9])([O-])=O>O.CO.C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[CH2:7][S:8]([NH:11][C:12]1[CH:13]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=[CH:16][CH:17]=1)(=[O:10])=[O:9]

참가 물질

6

반응물 1

HCID 86636267HCID 86636267, 화합물

생성물 1

HCID 57961598tert-Butyl (3-{[(3-aminobenzyl)sulfonyl]amino}phenyl)carbamate수율 90%

시약·촉매·용매 4

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 887Methanol용매HCID 962Water용매

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온도
0 °C

실험 절차

To a solution tert-butyl (3-{[(3-nitrobenzyl)sulfonyl]amino}phenyl)carbamate (1.1 g, 2.7 mmol) in water (2 mL), methanol (100 mL) and acetic acid (4.1 mL) was added iron (0.60 g, 11.0 mmol) powder in one batch. The mixture was stirred at 0° C. for 2 h. The mixture was mixed with celite, filtered, and the cake was washed with EtOAc. The brown filtrate was concentrated and EtOAc and NaHCO3/water were added. The water layer was extracted with EtOAc once more. The organic layers were combined, dried over Na2SO4 and concentrated to give the desired product as a yellow powder (0.9 g, 90%). LCMS for C18H23N3O4S (M-tBu+H)+: m/z=322.0. 1H NMR (400 MHz, DMSO-d6): δ 9.72 (s, 1H), 9.39 (s, 1H), 7.44 (br, 1H), 7.16 (t, J=8.2 Hz, 1H), 7.12 (m, 1H), 6.94 (t, J=7.7 Hz, 1H), 7.79 (dt, J=7.2, 2.1 Hz, 1H), 6.50 (m, 1H), 6.49 (s, 1H), 6.35 (m, 1H).

후처리

  1. additionThe mixture was mixed with celite
  2. filtrationfiltered
  3. washthe cake was washed with EtOAc
  4. concentrationThe brown filtrate was concentrated
  5. additionEtOAc and NaHCO3/water were added
  6. extractionThe water layer was extracted with EtOAc once more
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4551297eee1841c0af934854f5698d9a
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871753B2

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