Methyl chloroformate → Methyl 2-(Difluoromethyl)-4-(2-methylpropyl)-5-[(methoxycarbonyl)thio]-6-(trifluoromethyl)-3-pyridinecarboxylate

HRID 395397

반응식

HRID 395397 반응식
[F:1][CH:2]([F:22])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([SH:17])=[C:5]([C:18]([F:21])([F:20])[F:19])[N:4]=1.Cl[C:24]([O:26][CH3:27])=[O:25].C(N(CC)CC)C>C1COCC1>[F:22][CH:2]([F:1])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([S:17][C:24]([O:26][CH3:27])=[O:25])=[C:5]([C:18]([F:21])([F:20])[F:19])[N:4]=1

참가 물질

5

반응물 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 9974711Methyl 2-(difluoromethyl)-4-isobutyl-5-mercapto-6-(trifluoromethyl)-3-pyridinecarboxylate

생성물 1

HCID 22668810Methyl 2-(Difluoromethyl)-4-(2-methylpropyl)-5-[(methoxycarbonyl)thio]-6-(trifluoromethyl)-3-pyridinecarboxylate수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 3.05 g (0.0089 mol) of product of example 1 and 0.094 g (0.01 mol) of methyl chloroformate in 25 mL dry THF was added 1.16 g (0.012 mol) of triethylamine dropwise at room temperature. After stirring for 30 min, the solvent was evaporated under reduced pressure. The residue was diluted with 100 mL of water and extracted with ether (3×50 mL). The combined organic layers were washed with water, dried (MgSO4) and evaporated. Purification of the residue by preparative HPLC (5% ethyl acetate-hexane) gave 2.75 g (77%) of product as a yellow oil: nD25 1.5830.

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. additionThe residue was diluted with 100 mL of water
  3. extractionextracted with ether (3×50 mL)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customPurification of the residue by preparative HPLC (5% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-c25c17ef8907471f8ef0d0fd14a7ab5d
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06605624B1

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