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

HRID 60064
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 60064
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 1146TrimethylamineHCID 14798Sodium Hydroxide2×HCID 579431784-((S)-2-(4-ethylthiazol-2-yl)-2-((S)-2-(methoxycarbonylamino)-3-phenylpropanamido)ethyl)phenylsulfamic acidHCID 178503014HCID 178503014, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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%.

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-ee92d6c95e6f4f63adb8074df9cfbf5b
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09440963B2

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