Hydrochloric Acid → 5-[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]pentanoic acid

HRID 505293ノート

反応式

HRID 505293 の反応式
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([O:26][C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:22][C:21]=3[N:31]([CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH2:35][CH:36]=[O:37])[C@H:14]2[CH3:40])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CC(=CC)C.[O-:48]Cl=O.[Na+].Cl>C1COCC1.CC(O)(C)C.O.CCOC(C)=O>[F:42][C:2]([F:1])([F:41])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([O:26][C:27]([F:28])([F:29])[F:30])[CH:23]=[CH:22][C:21]=3[N:31]([CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH2:35][C:36]([OH:48])=[O:37])[C@H:14]2[CH3:40])[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 248965325-[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]pentanal

生成物 1

HCID 248965335-[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]pentanoic acid

試薬・触媒・溶媒 4

HCID 962Water溶媒2 回HCID 6386tert-Butanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 5-[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]pentanal (6.8 mg, 0.011 mmol) in THF (20 μL) and t-BuOH (60 μL) was added 2-methyl-2-butene (20 μL), followed by a solution of NaClO2 (3.0 mg, 0.024 mmol) and NaH2PO4 (3.5 mg, 0.024 mmol) in water (25 μL). The reaction was stirred at room temperature for 30 minutes and then diluted with EtOAc (8 mL) and water (2 mL), acidified with 1 N HCl (2 mL), and washed with brine (5 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by PTLC (EtOAc) afforded 5-[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]pentanoic acid. Rf=0.20 (EtOAc). LCMS=631.3 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.88 (s, 1H), 7.78 (s, 2H), 7.18-7.15 (m, 3H), 5.73 (d, J=8.0 Hz, 1H), 4.75 (d, J=16.5 Hz, 1H), 4.58 (m, 1H), 4.03 (s, 1H), 2.97 (m, 4H), 2.31 (t, J=7.3 Hz, 2H), 1.40-1.23 (m, 5H), 1.00 (t, J=6.7 Hz, 3H), 0.69 (d, J=6.4 Hz, 3H).

後処理

  1. washwashed with brine (5 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue by PTLC (EtOAc)

出典と根拠

ORDレコード
ord-bf61750d642742159ccdf7eb357c6cfd
出典データセット
uspto-grants-2010_08
特許番号
US07781426B2

反応ノート

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