Trifluoroacetic acid → dibenzyl ((2S,3S,5S)-3-hydroxy-1,6-diphenylhexane-2,5-diyl)dicarbamate

HRID 744750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 744750
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C@H:20]1[O:41][C@@H:21]1[C@@H:22]([NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].FC(F)(F)C(O)=O>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C@@H:20]([OH:41])[CH2:21][C@@H:22]([NH:30][C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 15384541(2S,3R,4R,5S)-2,5-bis-(N-(((benzyl)oxy)carbonyl)amino)-3,4-epoxy-1,6-diphenylhexane

Produkt 1

HCID 460972dibenzyl ((2S,3S,5S)-3-hydroxy-1,6-diphenylhexane-2,5-diyl)dicarbamateAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 39.2 g (71.2 mmol) of (2S,3R,4R,5S)-2,5-bis-(N-(((benzyl)oxy)carbonyl)amino)-3,4-epoxy-1,6-diphenylhexane in 600 ml of THF was treated under N2 atmosphere with 13 g (0.36 mol) of sodium borohydride. The resulting mixture was treated dropwise with 27.7 ml (0.36 mol) of trifluoroacetic acid. After being stirred for 3.5 h at ambient temperature, the resulting mixture was quenched with 1N aqueous HCl, diluted with water, and stirred for 16 h. The resulting mixture was filtered, washed with water, and dried to provide 22.85 g (58%) of the desired compound as a white solid.

Aufarbeitung

  1. customthe resulting mixture was quenched with 1N aqueous HCl
  2. additiondiluted with water
  3. stirringstirred for 16 h
  4. filtrationThe resulting mixture was filtered
  5. washwashed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-78d1395932ee40e9a3a6e9d1727d4f67
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05559158

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