Ethanol → (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-{(1-ethylpropoxy)[(4-hydroxyphenyl)sulfonyl]amino}-2-hydroxypropylcarbamate

HRID 29218

Reaktionsgleichung

Reaktionsgleichung von HRID 29218
[CH2:1]([C@H:8]([NH:36][C:37](=[O:47])[O:38][C@@H:39]1[C@H:46]2[C@H:42]([O:43][CH2:44][CH2:45]2)[O:41][CH2:40]1)[C@H:9]([OH:35])[CH2:10][N:11]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27]CC2C=CC=CC=2)=[CH:23][CH:22]=1)(=[O:20])=[O:19])[O:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C>[Pd].C(OCC)(=O)C>[CH2:1]([C@H:8]([NH:36][C:37](=[O:47])[O:38][C@@H:39]1[C@H:46]2[C@H:42]([O:43][CH2:44][CH2:45]2)[O:41][CH2:40]1)[C@H:9]([OH:35])[CH2:10][N:11]([O:12][CH:13]([CH2:14][CH3:15])[CH2:16][CH3:17])[S:18]([C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1)(=[O:20])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 702EthanolHCID 59090701(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-[([4-(benzyloxy)phenyl]sulfonyl}(1-ethylpropoxy)amino]-2-hydroxypropylcarbamate

Produkt 1

HCID 59090686(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-{(1-ethylpropoxy)[(4-hydroxyphenyl)sulfonyl]amino}-2-hydroxypropylcarbamateAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-[{[4-(benzyloxy)phenyl]sulfonyl}(1-ethylpropoxy)amino]-2-hydroxypropylcarbamate (222 mg, 0.384 mmol) in 3:1 absolute ethanol:ethyl acetate was combined with Palladium on carbon (10 wt %, 44 mg) and reduced under an atmosphere of Hydrogen gas over 16 hours. The reaction was filtered and evaporated in vacuo. The residue was purified on flash grade silica gel eluting with 3:2 ethyl acetate:hexane. Fractions containing the product were combined and evaporated in vacuo. The residue was triturated with water, filtered and dried under high vacuum to provide (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-{(1-ethylpropoxy)[(4-hydroxyphenyl)sulfonyl]amino}-2-hydroxypropylcarbamate (103 mg, 46%) as a white solid. H1-NMR (chloroform-D3): 0.91 (m, 6H), 1.61 (m, 7H), 2.93 (m, 5H), 3.70 (m, 2H), 3.92 (m, 4H), 4.17 (m, 1H), 4.79 (d, 1H), 5.01 (m, 1H), 5.66 (d, 1H), 6.12 (s, 1H), 6.94 (d, 2H), 7.26 (m, 5H), 7.72 (d, 2H). MS(ESI): 601(M+Na).

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. customevaporated in vacuo
  3. customThe residue was purified on flash grade silica gel eluting with 3:2 ethyl acetate
  4. additionFractions containing the product
  5. customevaporated in vacuo
  6. customThe residue was triturated with water
  7. filtrationfiltered
  8. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b505e9115bd74d3a99fba72982e33cfa
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419967B2

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