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

HRID 1182126ノート

反応式

HRID 1182126 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6a2481ef0ce647b6982b3063347f2b67
出典データセット
uspto-grants-2007_10
特許番号
US07288537B2

反応ノート

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