Hydrochloric Acid → (2S)-N-((1S,2S)-3-{(2S,3R)-2-[N-(tert-butyl)carbamoyl]-3-hydroxypyrrolidinyl}-2-hydroxy-3-oxo-1-benzylpropyl)-3-carbamoyl-2-[(phenylmethoxy)carbonylamino]propanamide

HRID 1780240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1780240
Cl.C(O[C:7]([N:9]1[CH2:20][CH2:19][C@@H:18]([O:21][Si](C(C)(C)C)(C)C)[C@H:10]1[C:11]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:8])(C)(C)C.[CH2:29]([O:36][C:37]([NH:39][C@H:40]([C:45]([NH:47][C@@H:48]([CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C@H:49]([OH:53])C(O)=O)=[O:46])[CH2:41][C:42](=[O:44])[NH2:43])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCOCC1.CO>[CH2:29]([O:36][C:37]([NH:39][C@H:40]([C:45]([NH:47][C@@H:48]([CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[C@H:49]([OH:53])[C:7]([N:9]1[CH2:20][CH2:19][C@@H:18]([OH:21])[C@H:10]1[C:11]([NH:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])=[O:8])=[O:46])[CH2:41][C:42](=[O:44])[NH2:43])=[O:38])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 22872710(3R)-1-t-butoxycarbonyl-N-t-butyl-3-t-butyldimethylsilyloxy-L-prolinamideHCID 57125825(2S,3S)-3-(N2-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyric acid

Produkt 1

HCID 473132(2S)-N-((1S,2S)-3-{(2S,3R)-2-[N-(tert-butyl)carbamoyl]-3-hydroxypyrrolidinyl}-2-hydroxy-3-oxo-1-benzylpropyl)-3-carbamoyl-2-[(phenylmethoxy)carbonylamino]propanamideAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1.5 ml of a 4N solution of hydrogen chloride in dioxane were added to a solution of 50 mg (0.13 mmol) of (3R)-1-t-butoxycarbonyl-N-t-butyl-3-t-butyldimethylsilyloxy-L-prolinamide (prepared as described in Preparation 12) in 0.5 ml of methanol, and the mixture was stirred at room temperature for 1 hour. The solvent was removed by distillation under reduced pressure, and the resulting residue was mixed with benzene. The excess hydrogen chloride was then removed by distillation as an azeotrope with the benzene. The resulting residue was dried in vacuo for 2 hours and the whole of the resulting (3E)-N-t-butyl-3-t-butyldimethylsilyloxy-L-prolinamide hydrochloride was reacted with 55 mg (0.13 mmol) of (2S,3S)-3-(N2 -benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyric acid (prepared as described in Preparation 1) following a procedure similar to that described in Example 1, to obtain 33 mg of the title compound as a white powder, melting at 109°-112° C.

Aufarbeitung

  1. customThe solvent was removed by distillation under reduced pressure
  2. additionthe resulting residue was mixed with benzene
  3. customThe excess hydrogen chloride was then removed by distillation as an azeotrope with the benzene
  4. customThe resulting residue was dried in vacuo for 2 hours

Quellen und Nachweise

ORD-Eintrag
ord-4974866c2f4c442fb06f2d9814afd204
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05629406

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