Borane;tetrahydrofuran → N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(hydroxymethyl)phenyl]-N-propylmethanesulfonamide

HRID 899455노트

반응식

HRID 899455 반응식
C(OC([NH:8][C:9]([CH3:37])([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:10][O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([N:22]([S:26]([CH3:29])(=[O:28])=[O:27])[CH2:23][CH2:24][CH3:25])[CH:21]=1)[C:16](O)=[O:17])=O)(C)(C)C.B.C1COCC1>C1COCC1>[NH2:8][C:9]([CH3:37])([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:10][O:11][CH2:12][C:13]1[CH:21]=[C:20]([N:22]([CH2:23][CH2:24][CH3:25])[S:26]([CH3:29])(=[O:28])=[O:27])[CH:19]=[C:15]([CH2:16][OH:17])[CH:14]=1

참가 물질

4

반응물 2

HCID 2723981Borane;tetrahydrofuranHCID 588563373-({2-[(Tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid2회

생성물 1

HCID 67319197N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(hydroxymethyl)phenyl]-N-propylmethanesulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3({2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid (intermediate XI, 145 mg, 0.271 mmol) in THF (2 mL) cooled to 0° C. was added BH3-THF (1.356 mL, 1.356 mmol, 1 M in THP). After 10 min, the reaction mixture was allowed to warm to rt and stirred for 60 h. The reaction mixture was cooled back down to 0° C. and carefully quenched with MeOH. The mixture was concentrated to half its original volume and diluted with EtOAc and water. Following dilution, the organic layer was extracted, washed with sat. aq. NaHCO3 and brine, dried over sodium sulfate and concentrated in vacuo to provide N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(hydroxymethyl)phenyl]-N-propylmethanesulfonamide as a white foam. 1H NMR (400 MHz, CDCl3) δ 7.33 (s, 1H), 7.29 (s, 1H), 7.28-7.20 (m, 4H), 7.17-7.13 (m, 2H), 4.74 (s, 2H), 4.60-4.51 (m, 3H), 3.63 (t, J=7.2 Hz, 2H), 3.53 (A of AB, d, J=8.8 Hz, 1H), 3.43 (B of AB, d, J=8.8 Hz, 1H), 3.12 (A of AB, d, J=13.2 Hz, 1H), 2.93 (B of AB, d, J=13.2 Hz, 1H), 2.88 (s, 3H), 1.55-1.45 (m, 2H), 1.46 (s, 9H), 1.25 (s, 3H), 0.91 (t, J=7.3 Hz, 3H).

후처리

  1. temperatureThe reaction mixture was cooled back down to 0° C.
  2. customcarefully quenched with MeOH
  3. concentrationThe mixture was concentrated to half its original volume
  4. additiondiluted with EtOAc and water
  5. extractionthe organic layer was extracted
  6. washwashed with sat. aq. NaHCO3 and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e2bb77e9b5424f92a2f3bc4f0f32fd3e
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354942B2

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