Water → Efavirenz

HRID 389410

反応式

HRID 389410 の反応式
C([O-])([O-])=O.[K+].[K+].C(=O)(OC(Cl)C)[O:8][C@:9]([C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[NH:26][C:27]([C@@]12C(C)(C)[C@@](C)(CC1)C(=O)O2)=[O:28])([C:14]#[C:15][CH:16]1[CH2:18][CH2:17]1)[C:10]([F:13])([F:12])[F:11].C(OC)(C)(C)C.O>CN(C)C=O>[Cl:25][C:23]1[CH:22]=[CH:21][C:20]2[NH:26][C:27](=[O:28])[O:8][C@:9]([C:14]#[C:15][CH:16]3[CH2:18][CH2:17]3)([C:10]([F:13])([F:12])[F:11])[C:19]=2[CH:24]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 66889351(S)-2-(5-chloro-2-((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamido) phenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-yl 1-chloroethyl carbonate

生成物 1

HCID 64139Efavirenz

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

K2CO3 (13.3 g, 95.8 mmol) powder was added to a solution of (S)-2-(5-chloro-2-((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamido) phenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-yl 1-chloroethyl carbonate (7, R1 is 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptyl, R3 is 1-chloroethyl, 36.8 g, 63.9 mmol) in N,N-dimethylformamide (150 mL). The reaction mixture was stirred at room temperature overnight. Methyl t-butyl ether (300 mL) and water (300 mL) were added to the mixture, and the resulting layers were separated. The organic layer was washed with brine and evaporated to 60 mL then petroleum ether (200 mL) was added. The resulting mixture was filtered and rinsed with petroleum ether to give (S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one (Efavirenz, 1) as an off-white solid.

後処理

  1. customthe resulting layers were separated
  2. washThe organic layer was washed with brine
  3. customevaporated to 60 mL
  4. additionpetroleum ether (200 mL) was added
  5. filtrationThe resulting mixture was filtered
  6. washrinsed with petroleum ether

出典と根拠

ORDレコード
ord-4cb4a8370be842d6a0713f5cfb110e2d
出典データセット
uspto-grants-2013_02
特許番号
US08378143B2

関連ノート

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