Sodium Hydroxide → N-[(S)-2-(5-Bromo-2-fluoro-phenyl)-2-hydroxy-propyl]-2-nitro-benzenesulfonamide

HRID 39233

반응식

HRID 39233 반응식
[NH2:1][CH2:2][C@:3]([C:6]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:7]=1[F:13])([OH:5])[CH3:4].[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24])([O-:16])=[O:15].[OH-].[Na+]>C1COCC1.CC(OC)(C)C>[Br:12][C:10]1[CH:9]=[CH:8][C:7]([F:13])=[C:6]([C@@:3]([OH:5])([CH3:4])[CH2:2][NH:1][S:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N+:14]([O-:16])=[O:15])(=[O:24])=[O:25])[CH:11]=1

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 155402-Nitrobenzenesulfonyl chlorideHCID 66666122(S)-1-Amino-2-(5-bromo-2-fluoro-phenyl)-propan-2-ol

생성물 1

HCID 66665841N-[(S)-2-(5-Bromo-2-fluoro-phenyl)-2-hydroxy-propyl]-2-nitro-benzenesulfonamide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 15413tert-Butyl methyl ether용매

반응 조건

온도
20 °C

실험 절차

To a solution of (S)-1-amino-2-(5-bromo-2-fluoro-phenyl)-propan-2-ol (34.7 g, 140 mmol) in THF (400 ml) was added 2-nitro-benzenesulfonyl chloride (34.9 g, 154 mmol) at 0-5° C. and afterwards 1N aqueous NaOH over a period of 0.5 h. The reaction mixture was stirred for 2 h at 20° C. The reaction mixture was diluted with TBME and washed with water and NaH2PO4 solution and brine, dried over MgSO4, filtered and concentrated to provide the title compound after crystallization from TBME-hexane as beige crystals: TLC (toluene-EtOAc 3:1): Rf=0.51; UPLC RtH5=1.118 min; ESIMS: 450, 452 [(M+NHa)+]; 1H NMR (360 MHz, CDCl3): δ 7.98 (m, 1H), 7.81 (m, 1H), 7.65 (m, 2H), 7.59 (dd, 1H), 7.24 (m, 1H), 6.79 (dd, 1H), 5.60 (t, 1H), 4.16 (br s, 1H), 3.55 (dd, 1H), 3.44 (dd, 1H), 2.51 (s, 1H), 1.51 (s, 3H).

후처리

  1. washwashed with water and NaH2PO4 solution and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e74ab5290fe748a98af7c35364079e35
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524897B2

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