Triethylamine → HCID 57974061、化合物

HRID 1864812ノート

反応式

HRID 1864812 の反応式
C([S@@]([NH:7][C@H:8]([C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=1)[CH2:9][CH2:10][C:11]([CH3:17])([CH3:16])[C:12](OC)=[O:13])=O)(C)(C)C.C(N(CC)CC)C>CO>[F:25][C:20]1[CH:19]=[C:18]([C@H:8]2[NH:7][C:12](=[O:13])[C:11]([CH3:17])([CH3:16])[CH2:10][CH2:9]2)[CH:23]=[C:22]([F:24])[CH:21]=1

参加物

4

反応物 2

HCID 8471TriethylamineHCID 66864959Methyl (δS)-δ-[[(S)-(1,1-dimethylethyl)sulfinyl]amino]-3,5-difluoro-α,α-dimethylbenzenepentanoate

生成物 1

HCID 57974061HCID 57974061、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
65 °C

実験手順

A solution of methyl (5S)-5-{[(S)-tert-butylsulfinyl]amino}-5-(3,5-difluorophenyl)-2,2-dimethylpentanoate from Step E (300. mg, 0.800 mmol) in MeOH (16 mL) was cooled to 0° C. Hydrogen chloride gas (anhydrous) was bubbled through this cold solution for about 30 seconds, after which time the reaction vessel was sealed and allowed to sit in the ice bath for 15 minutes. Dry nitrogen was then bubbled through the solution for 30 minutes, prior to removal of solvent in vacuo. More MeOH (˜50 mL) was added, and then removed in vacuo. After dissolving in a third volume of MeOH (16 mL), triethylamine (323 mg, 3.2 mmol) was introduced and the mixture was heated to 65° C. for 16 hours. After cooling to ambient temperature, the solvent was removed in vacuo and the residue was partitioned between diethyl ether (50 mL) and 1 M HCl (50 mL). The organics were washed with additional 1 M HCl (50 mL), water (50 mL) and saturated brine (50 mL). The ethereal solution was dried over sodium sulfate, filtered and then concentrated in vacuo to provide the title compound, which could be used without further purification. MS: m/z=240 (M+1).

後処理

  1. customHydrogen chloride gas (anhydrous) was bubbled through this cold solution for about 30 seconds
  2. customafter which time the reaction vessel was sealed
  3. customDry nitrogen was then bubbled through the solution for 30 minutes
  4. customto removal of solvent in vacuo
  5. additionMore MeOH (˜50 mL) was added
  6. customremoved in vacuo
  7. additionwas introduced
  8. temperatureAfter cooling to ambient temperature
  9. customthe solvent was removed in vacuo
  10. customthe residue was partitioned between diethyl ether (50 mL) and 1 M HCl (50 mL)
  11. washThe organics were washed with additional 1 M HCl (50 mL), water (50 mL) and saturated brine (50 mL)
  12. dry with materialThe ethereal solution was dried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6736814cce5042419d0d9f5bc9f29e77
出典データセット
uspto-grants-2009_12
特許番号
US07625901B2

反応ノート

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