Trifluoroacetic acid → HCID 178487211、化合物

HRID 2202297ノート

反応式

HRID 2202297 の反応式
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([NH:20][C:21]([C@H:23]2[C:32]3[C:27](=[CH:28][C:29]([O:33][CH3:34])=[CH:30][CH:31]=3)[CH2:26][CH2:25][N:24]2[C:35]([C@@H:37]2[CH2:40][C@H:39]([CH2:41][C:42]([O:44]C(C)(C)C)=[O:43])[CH2:38]2)=[O:36])=[O:22])[CH:12]=[C:13]([F:19])[C:14]=1[Si:15]([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])O.[Na+]>>[F:8][C:9]1[CH:10]=[C:11]([NH:20][C:21]([C@H:23]2[C:32]3[C:27](=[CH:28][C:29]([O:33][CH3:34])=[CH:30][CH:31]=3)[CH2:26][CH2:25][N:24]2[C:35]([C@@H:37]2[CH2:40][C@H:39]([CH2:41][C:42]([OH:44])=[O:43])[CH2:38]2)=[O:36])=[O:22])[CH:12]=[C:13]([F:19])[C:14]=1[Si:15]([CH3:17])([CH3:18])[CH3:16]

参加物

4

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 178487215HCID 178487215、化合物

生成物 1

HCID 178487211HCID 178487211、化合物収率 66.4%

反応条件

温度
0 °C

実験手順

Cooled TFA (2 mL) was added to tert-butyl 2-(cis-3-((R)-1-((3,5-difluoro-4-(trimethylsilyl)phenyl)carbamoyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)cyclobutyl)acetate (130 mg, 0.22 mmol) at 0° C., and the mixture was stirred at 0° C. for 30 min. The pH of the reaction mixture was adjusted to 6 with cooled aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 50→100% ethyl acetate/hexane) to give the title compound (78 mg, 0.146 mmol, 65.9%) as a white solid.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 50→100% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-2ebf9a902f2e452184d178b17841b63b
出典データセット
uspto-grants-2016_06
特許番号
US09365520B2

反応ノート

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