Ammonium Hydroxide → HCID 58550623、化合物

HRID 1890710ノート

反応式

HRID 1890710 の反応式
[O:1]=[C:2]1[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@@:3]21[CH2:34][C:21]1=[N:22][C:23]3[CH:24]=[CH:25][C:26]([C:30](NN)=[O:31])=[CH:27][C:28]=3[CH:29]=[C:20]1[CH2:19]2.[NH4+].[OH-]>C(Cl)Cl.O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[O:1]=[C:2]1[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@@:3]21[CH2:34][C:21]1=[N:22][C:23]3[CH:24]=[CH:25][C:26]([CH:30]=[O:31])=[CH:27][C:28]=3[CH:29]=[C:20]1[CH2:19]2

参加物

6

反応物 2

HCID 14923Ammonium HydroxideHCID 58550577HCID 58550577、化合物

生成物 1

HCID 58550623HCID 58550623、化合物

試薬・触媒・溶媒 3

HCID 178511488HCID 178511488、化合物触媒HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒2 回

実験手順

To a rapidly stirred solution of (2S)-2′-oxo-1′-{[2-(trimethylsilyl)eth-oxy]methyl}-1,1′,2′,3-tetrahydrospiro[cyclopenta[b]quinoline-2,3′-pyrrolo[2,3-b]pyridine]-7-carbohydrazide from Step H (317 mg, 0.667 mmol) in DCM (6.8 mL) was added water (2.7 mL) plus concentrated aqueous NH4OH (0.6 mL) and lastly potassium ferricyanide (549 mg, 1.67 mmol). After 4.5 hours the reaction was diluted with water (20 mL) and DCM (40 mL). The aqueous layer was extracted once with DCM (20 mL). The combined organics were washed successively with water then half-saturated brine and then dried over sodium sulfate. The organics were then filtered, concentrated in vacuo, and applied to a silica gel column for purification, eluting with a gradient of CH2Cl2:MeOH—99:1 to 90:10. Clean product-containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=446 (M+1).

後処理

  1. extractionThe aqueous layer was extracted once with DCM (20 mL)
  2. washThe combined organics were washed successively with water
  3. dry with materialhalf-saturated brine and then dried over sodium sulfate
  4. filtrationThe organics were then filtered
  5. concentrationconcentrated in vacuo
  6. customapplied to a silica gel column for purification
  7. washeluting with a gradient of CH2Cl2
  8. additionClean product-containing fractions
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-fac5351aa7804aa2bbc8b30e6fc12639
出典データセット
uspto-grants-2013_08
特許番号
US08507477B2

反応ノート

読み込み中…