Trifluoroacetic acid → N-{(S)-3-[3-(4-fluorophenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-3,4,5-trimethoxy-benzamide

HRID 1182126노트

반응식

HRID 1182126 반응식
C([O:5][CH2:6][C@@H:7]([NH:22][C:23](=[O:36])[C:24]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=1)[CH2:8][CH2:9][N:10]1[CH2:13][CH:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:11]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH:12]2[CH2:11][N:10]([CH2:9][CH2:8][C@H:7]([NH:22][C:23](=[O:36])[C:24]3[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=3)[CH2:6][OH:5])[CH2:13]2)=[CH:16][CH:17]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 10289176N-{(S)-1-tert-butoxymethyl-3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propyl}-3,4,5-trimethoxy-benzamide

생성물 1

HCID 10310458N-{(S)-3-[3-(4-fluorophenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-3,4,5-trimethoxy-benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of N-{(S)-1-tert-butoxymethyl-3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propyl}-3,4,5-trimethoxy-benzamide (Example 1, 0.066 g, 0.130 mmol) in dichloromethane (2 ml) is treated with trifluoroacetic acid (0.11 ml, 0.65 mmol) and the reaction mixture stirred for 20 hours. The solvent is evaporated and the residue partitioned between ethylacetate and saturated aqueous NaHCO3. The ethylacetate phase is washed with brine, dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography (elution 100% ethylacetate then 5:95 methanol/dichloromethane) to afford N-{(S)-3-[3-(4-fluorophenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-3,4,5-trimethoxy-benzamide [MH]+ 449.1.

후처리

  1. customThe solvent is evaporated
  2. customthe residue partitioned between ethylacetate and saturated aqueous NaHCO3
  3. washThe ethylacetate phase is washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe crude product is purified by flash silica chromatography (
  7. washelution 100% ethylacetate

출처 및 근거

ORD 기록
ord-6a2481ef0ce647b6982b3063347f2b67
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288537B2

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