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Hydrochloric Acid → 4-(tert-butoxycarbonylamino-methyl)-benzoic acid (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester

HRID 2187100
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2187100
[CH2:1]([C@H:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][C@H:9]1[OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([O:31][C:32]([NH:34][CH2:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][CH:37]=1)=[O:33])([CH3:30])([CH3:29])[CH3:28].Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([C@H:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:40](=[O:41])[C:39]3[CH:38]=[CH:37][C:36]([CH2:35][NH:34][C:32]([O:31][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:33])=[CH:44][CH:43]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][C@H:9]1[OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 8536054-(((tert-Butoxycarbonyl)amino)methyl)benzoic acidHCID 9885963(3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenol

Produkt 1

HCID 865847964-(tert-butoxycarbonylamino-methyl)-benzoic acid (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl esterAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 500 mg (1.33 mmol) (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenol in 10 ml methylenechloride were added 368 mg (1.46 mmol) 4-(tert-butoxycarbonylamino-methyl)-benzoic acid, 16.3 mg (0.133 mmol) DMAP und 511 mg (2.66 mmol) N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and the reaction mixture was stirred at 0° C. After 1 hour, 0.5 N HCl was added and the aqueous layer was extracted with methylenechloride. The combined organic layers were washed with 0.5N HCl solution and brine, dried over NaSO4, filtered and the solvent was removed under reduced pressure to give the crude product. Crystallization from diethylether yielded 280 mg (0.460 mmol, 35%) 4-(tert-butoxycarbonylamino-methyl)-benzoic acid (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester as colorless crystalls.

Aufarbeitung

  1. extractionthe aqueous layer was extracted with methylenechloride
  2. washThe combined organic layers were washed with 0.5N HCl solution and brine
  3. dry with materialdried over NaSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customto give the crude product
  7. customCrystallization from diethylether

Quellen und Nachweise

ORD-Eintrag
ord-9253fe28a25b4c058f7e54a064c85b26
Quelldatensatz
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06407235B1

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