Acetic Acid → (S)-tert-Butyl 3-(3-formylphenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate

HRID 1471635ノート

反応式

HRID 1471635 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C@H:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])=[O:12])[CH:6]=[CH:7][CH:8]=1)#N.C(O)(=[O:33])C>N1C=CC=CC=1.[Ni].O>[CH:1]([C:3]1[CH:4]=[C:5]([CH2:9][C@H:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])=[O:12])[CH:6]=[CH:7][CH:8]=1)=[O:33]

参加物

6

反応物 2

HCID 176Acetic AcidHCID 90289954(S)-tert-Butyl 3-(3-cyanophenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate

生成物 1

HCID 90289977(S)-tert-Butyl 3-(3-formylphenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 962Water溶媒HCID 1049Pyridine溶媒

反応条件

温度
46 °C

実験手順

(S)-tert-Butyl 3-(3-cyanophenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (2.7 g, 6.60 mmole) was dissolved in pyridine (18.6 ml) and acetic acid (9.3 ml). Raney Nickel (2.7 g of a slurry in H2O) was added and the resulting suspension was stirred at 46° C. overnight. The reaction was confirmed complete by reverse phase HPLC/MS. The reaction was cooled to room temperature and then filtered through celite. The filtrate was concentrated under reduced pressure and then partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (3×). The combined organics were washed with H2O (2×) and brine (2×). The organic layer was dried over MgSO4, filtered and concentrated. The crude produce was dried under high vacuum overnight and used without further purification. Yield was 2.70 g. MS (m/z) 413 [M+H]+.

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. custompartitioned between EtOAc and H2O
  5. extractionThe aqueous layer was extracted with EtOAc (3×)
  6. washThe combined organics were washed with H2O (2×) and brine (2×)
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude produce
  11. customwas dried under high vacuum overnight
  12. customused without further purification

出典と根拠

ORDレコード
ord-3f957aff861d47c59aed697c6cfed68a
出典データセット
uspto-grants-2015_04
特許番号
US09012441B2

反応ノート

読み込み中…