(R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((R)-2,3-bis(octylcarbamoyloxy)propylthio)propanoate → (R)-2-(benzyloxycarbonylamino)-3-((R)-2,3-bis(octylcarbamoyloxy)propylthio)propanoic acid

HRID 2205059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2205059
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:20][S:21][CH2:22][C@H:23]([O:37][C:38](=[O:48])[NH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:24][O:25][C:26](=[O:36])[NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:13]([O:15]C(C)(C)C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:20][S:21][CH2:22][C@H:23]([O:37][C:38](=[O:48])[NH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:24][O:25][C:26](=[O:36])[NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 71294581(R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((R)-2,3-bis(octylcarbamoyloxy)propylthio)propanoate

Produkt 1

HCID 67401308(R)-2-(benzyloxycarbonylamino)-3-((R)-2,3-bis(octylcarbamoyloxy)propylthio)propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of (R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((R)-2,3-bis(octylcarbamoyloxy)propylthio)propanoate in 30% TFA in DCM (0.3 M) was stirred at room temperature until complete deprotection of the tert-butyl group (4 hours). The reaction was diluted with DCM and concentrated with a stream of nitrogen. The reaction mixture was then diluted in MTBE and washed once with 1M citric acid (adjusted to pH3). The organic layer was dried over anhydrous Na2SO4 and concentrated en vaccuo. The resulting waxy solid was used without further purification.

Aufarbeitung

  1. concentrationconcentrated with a stream of nitrogen
  2. additionThe reaction mixture was then diluted in MTBE
  3. washwashed once with 1M citric acid (adjusted to pH3)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated en vaccuo
  6. customThe resulting waxy solid was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-5733b65788824dc6b3d4a7ebcdbe2f40
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365506B2

Notizen zur Reaktion

Wird geladen…