Dichloromethane → (R)-3-(2-(acetoxymethyl)-4-amino-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate

HRID 2378904ノート

反応式

HRID 2378904 の反応式
[C:1]([O:9][C@H:10]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22]C(OC(C)(C)C)=O)=[C:18]([CH3:30])[C:17]=1[CH2:31][O:32][C:33](=[O:35])[CH3:34])[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.FC(F)(F)C(O)=O>>[C:1]([O:9][C@H:10]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([CH3:30])[C:17]=1[CH2:31][O:32][C:33](=[O:35])[CH3:34])[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59732072(R)-3-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate

生成物 1

HCID 59732065(R)-3-(2-(acetoxymethyl)-4-amino-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate収率 97%

実験手順

(R)-3-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate (19.5 g, 40.2 mmol) in dichloromethane (100.00 ml, 1554 mmol) was added trifluoroacetic acid (30.00 ml, 389 mmol). The reaction mixture was stirred at RT. After 4 h, LC-MS suggested complete removal of protecting group. The solvent was removed and the crude product was dissolved in dichloromethane (300 mL) and washed with aqueous NaHCO3. The solvent was removed to give (R)-3-(2-(acetoxymethyl)-4-amino-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate (15.0 g, 38.9 mmol, 97% yield). MS (ESI) 408 (M+H); Rf=1.69.

後処理

  1. customremoval
  2. customThe solvent was removed
  3. dissolutionthe crude product was dissolved in dichloromethane (300 mL)
  4. washwashed with aqueous NaHCO3
  5. customThe solvent was removed

出典と根拠

ORDレコード
ord-5fc1e07634d94419aef2a00ff796d36c
出典データセット
uspto-grants-2008_12
特許番号
US07470680B2

反応ノート

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