Hydrochloric Acid → 4-{[(2-Fluoro-4-hydroxy-6-methyl-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic acid methyl ester

HRID 2261837ノート

反応式

HRID 2261837 の反応式
[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([O:20][Si](C(C)C)(C(C)C)C(C)C)=[CH:15][C:14]=2[F:31])[CH3:12])=[CH:6][C:5]=1[CH3:32].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1>[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([OH:20])=[CH:15][C:14]=2[F:31])[CH3:12])=[CH:6][C:5]=1[CH3:32]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 574433494-{[(2-Fluoro-6-methyl-4-triisopropylsilanyloxy-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic acid methyl ester

生成物 1

HCID 675280644-{[(2-Fluoro-4-hydroxy-6-methyl-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic acid methyl ester収率 76.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A mixture of 4-{[(2-fluoro-6-methyl-4-triisopropylsilanyloxy-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic acid methyl ester (457 mg, 0.965 mmol) and tetrabutylammonium fluoride (2.0 mL of 1M in THF, 2.0 mmol) in THF (10 mL) is stirred at 0° C. for 20 minutes and then 2.0 mL of 1M HCl is added and the mixture is concentrated. The residue is portioned between ethyl acetate and brine. The layers are separated and the brine layer is extracted with ethyl acetate. The combined ethyl acetate layers are dried (MgSO4) and concentrated. The residue is purified on 40 g silica with ethyl acetate in heptane gradient (10% to 70%) to provide 233 mg (76%) of the titled compound as a glass. LC-ES/MS m/e 318.2 (M+1).

後処理

  1. concentrationthe mixture is concentrated
  2. customThe layers are separated
  3. extractionthe brine layer is extracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate layers are dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is purified on 40 g silica with ethyl acetate in heptane gradient (10% to 70%)

出典と根拠

ORDレコード
ord-f2758d59b18d41259792b9ea7dad92b1
出典データセット
uspto-grants-2010_12
特許番号
US07846960B2

反応ノート

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