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

HRID 272290

반응식

HRID 272290 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-962c50109af24cc18087ea9ddcff22ab
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456157B2

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