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

HRID 1007235

反応式

HRID 1007235 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-227e2c56fc7840fe872762168c1bab43
出典データセット
uspto-grants-2004_09
特許番号
US06794396B2

関連ノート

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