Water → Efavirenz

HRID 659728

反応式

HRID 659728 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-ben zoxazin-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-aaaa6101172442a388d13d34a1122125
出典データセット
uspto-grants-2011_12
特許番号
US08080655B2

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