Water → Dimethyl 7-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]-3-t-butoxycarbonylamino-3-hydroxymethylheptylphosphonate

HRID 272290

Reaktionsgleichung

Reaktionsgleichung von HRID 272290
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]([NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])([CH2:35][O:36][Si](C(C)(C)C)(C)C)[CH:27]=[CH:28][P:29](=[O:34])([O:32][CH3:33])[O:30][CH3:31])=[C:18]([Cl:52])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O1CCCC1.O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]([NH:44][C:45]([O:47][C:48]([CH3:50])([CH3:49])[CH3:51])=[O:46])([CH2:35][OH:36])[CH2:27][CH2:28][P:29](=[O:34])([O:32][CH3:33])[O:30][CH3:31])=[C:18]([Cl:52])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 131727196Dimethyl 7-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]-3-t-butoxycarbonylamino-3-t-butyldimethylsiloxymethyl-1-heptenylphosphonate

Produkt 1

HCID 23094230Dimethyl 7-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]-3-t-butoxycarbonylamino-3-hydroxymethylheptylphosphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The compound of Example 287 was reduced in the same manner as in Reference Example 123 and the resulting compound (107 mg) was dissolved in tetrahydrofuran (5.0 mL). A 1 mol/L TBAF-tetrahydrofuran solution (160 μL) was added dropwise and the mixture was stirred for 3 hours at room temperature. Subsequently, water was added and the reaction mixture was extracted with ethyl acetate. The extract was washed sequentially with water and a saturated aqueous solution of sodium chloride and the organic phase was dried over anhydrous sodium sulfate. The solvent was removed by distillation and the residue was purified on a silica gel column chromatography (ethyl acetate only) to obtain the desired product as a colorless oil (47 mg).

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed sequentially with water
  3. dry with materiala saturated aqueous solution of sodium chloride and the organic phase was dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation
  5. customthe residue was purified on a silica gel column chromatography (ethyl acetate only)

Quellen und Nachweise

ORD-Eintrag
ord-962c50109af24cc18087ea9ddcff22ab
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456157B2

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