Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-isopropoxy-acetate → Ethyl 2-(2-aminothiazol-4-yl)-2-isopropoxy-acetate

HRID 524412ノート

反応式

HRID 524412 の反応式
C(OC([N:8](CC1C=CC(OC)=CC=1)[C:9]1[S:10][CH:11]=[C:12]([CH:14]([O:20][CH:21]([CH3:23])[CH3:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:8][C:9]1[S:10][CH:11]=[C:12]([CH:14]([O:20][CH:21]([CH3:22])[CH3:23])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1

参加物

3

反応物 1

HCID 68182441Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-isopropoxy-acetate

生成物 1

HCID 86669546Ethyl 2-(2-aminothiazol-4-yl)-2-isopropoxy-acetate収率 75%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-isopropoxy-acetate (0.55 g, 1.2 mmol) was dissolved in TFA (7 mL). The reaction mixture was refluxed for 5 hours. TFA was removed under reduced pressure. The residue was diluted with water (10 mL) and ethyl acetate (15 mL) and basified with sodium bicarbonate. The organic layer was separated and aqueous layer was again extracted with ethyl acetate (15 mL). The combined organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure to obtain crude product which was purified by silica gel column chromatography using 20% ethyl acetate in hexane to provide ethyl 2-(2-aminothiazol-4-yl)-2-isopropoxy-acetate (0.22 g).

後処理

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. customTFA was removed under reduced pressure
  3. additionThe residue was diluted with water (10 mL) and ethyl acetate (15 mL)
  4. customThe organic layer was separated
  5. extractionaqueous layer was again extracted with ethyl acetate (15 mL)
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customto obtain crude product which
  10. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b13024cc75f94df3a5a9b41b2a08af00
出典データセット
uspto-grants-2016_05
特許番号
US09340506B2

反応ノート

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