Trimethylamine → sodium 4-{(S)-2-(4-Ethylthiazol-2-yl)-2-[(S)-2-(methoxycarbonyl-amino)-3-phenyl-propanamido]ethyl}phenylsulfamate

HRID 60064

반응식

HRID 60064 반응식
[CH2:1]([C:3]1[N:4]=[C:5]([C@@H:8]([NH:21][C:22](=[O:36])[C@@H:23]([NH:31][C:32]([O:34][CH3:35])=[O:33])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17](=[O:20])(=[O:19])[OH:18])=[CH:12][CH:11]=2)[S:6][CH:7]=1)[CH3:2].[OH-].[Na+].N(C)(C)C.COS(O[Na:49])(=O)=O>CO.O>[CH2:1]([C:3]1[N:4]=[C:5]([C@@H:8]([NH:21][C:22](=[O:36])[C@@H:23]([NH:31][C:32]([O:34][CH3:35])=[O:33])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17](=[O:18])(=[O:19])[O-:20])=[CH:12][CH:11]=2)[S:6][CH:7]=1)[CH3:2].[Na+:49]

참가 물질

7

반응물 4

HCID 1146TrimethylamineHCID 14798Sodium Hydroxide2회HCID 579431784-((S)-2-(4-ethylthiazol-2-yl)-2-((S)-2-(methoxycarbonylamino)-3-phenylpropanamido)ethyl)phenylsulfamic acidHCID 178503014HCID 178503014, 화합물

생성물 1

HCID 90404193sodium 4-{(S)-2-(4-Ethylthiazol-2-yl)-2-[(S)-2-(methoxycarbonyl-amino)-3-phenyl-propanamido]ethyl}phenylsulfamate수율 83%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a solution of 4-((S)-2-(4-ethylthiazol-2-yl)-2-((S)-2-(methoxycarbonylamino)-3-phenylpropanamido)ethyl)-phenylsulfamic acid (75) (150 g, 0.272 mmol) in methanol (1.2 L) was added 50% NaOH (11.3 g, 0.272 mol, 1.0 equiv.) at room temperature. The resulting mixture was stirred at rt for 30 min and then concentrated under reduced pressure to give the crude product, which contained a small amount of Me3N and MeOSO3Na. To a stirred slurry of the crude product (75 g) in H2O (150 mL) was added aq. NaOH (2 g, 0.05 mol; in 50 mL H2O) in dropwise at room temperature. The slurry was continued to stir for 20 min, filtered and washed with water (10 mL) and ethyl ether (50 mL). Then the filter cake was dried under reduced pressure at 50° C. to give 62 g (83%) of the desired compound. LC/MS (M−1): 531; H-NMR (300 MHz, CD3OD) δ: 7.21-6.98 (m, 10H), 5.40-5.36 (t, 1H, J=6.9 Hz), 4.38-4.34 (t, 1H, J=7.5 Hz), 3.61 (s, 3H), 3.24-3.23 (m, 1H), 3.11-3.01 (m, 2H), 2.81-2.74 (m, 3H), 1.31-1.26 (t, 3H, J=7.5 Hz); HPLC: 98.5%.

후처리

  1. concentrationconcentrated under reduced pressure
  2. customto give the crude product, which
  3. stirringto stir for 20 min
  4. filtrationfiltered
  5. washwashed with water (10 mL) and ethyl ether (50 mL)
  6. customThen the filter cake was dried under reduced pressure at 50° C.

출처 및 근거

ORD 기록
ord-ee92d6c95e6f4f63adb8074df9cfbf5b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440963B2

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