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

HRID 2356238Notes

Reaction equation

HRID 2356238 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-ccd1bf4bf11d4a228f117d5cb4807113
Source dataset
uspto-grants-2010_07
Patent number
US07759326B2

Reaction notes

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