Water → Efavirenz

HRID 389410

반응식

HRID 389410 반응식
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

참가 물질

6

반응물 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

생성물 1

HCID 64139Efavirenz

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4cb4a8370be842d6a0713f5cfb110e2d
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08378143B2

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