Ethyl chloroformate → HCID 22710460、化合物

HRID 1061077ノート

反応式

HRID 1061077 の反応式
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]3[S:25][C:26]4[CH2:27][NH:28][CH2:29][CH2:30][C:31]=4[N:32]=3)=[O:23])[CH2:18][CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.O.[C:34](O)(=O)[CH:35]=[O:36].ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.O.C(N(CC)CC)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:17][CH2:18][N:19]([C:22]([C:24]3[S:25][C:26]4[CH2:27][NH:28][CH:29]([CH2:34][CH2:35][OH:36])[CH2:30][C:31]=4[N:32]=3)=[O:23])[CH2:20][CH2:21]1)(=[O:14])=[O:15])[CH:7]=[CH:6]2

参加物

8

反応物 4

HCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 11272253HCID 11272253、化合物HCID 15620607Glyoxylic acid, monohydrate

生成物 1

HCID 22710460HCID 22710460、化合物収率 72.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

In a similar manner to Example 91 except for the use of 1-[(6-chloronaphthalen-2-yl)sulfonyl]-4-[(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine hydrochloride (132 mg) and glyoxylic acid hydrate (82 mg) as the raw materials, the reaction was conducted, whereby a crude product was obtained. The product was suspended in tetrahydrofuran (50 ml), followed by the addition of triethylamine (0.22 ml) and ethyl chloroformate (0.03 ml) under ice cooling. After stirring at room temperature for 15 minutes, sodium borohydride (50 mg) and water (10 ml) were added and the resulting mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure. The concentrate was diluted with dichloromethane, washed with saturated saline and then dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (dichloromethane˜dichloromethane:methanol=100:3). The purified product was dissolved in saturated ethanol hydrochloride (1 ml), followed by concentration under reduced pressure. The concentrate was pulverized and washed in ethyl acetate, whereby the title compound (52 mg, 33%) was obtained.

後処理

  1. customwhereby a crude product was obtained
  2. stirringthe resulting mixture was stirred at room temperature for one hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionThe concentrate was diluted with dichloromethane
  5. washwashed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe residue obtained
  8. distillationby distilling off the solvent under reduced pressure
  9. customwas purified by chromatography on a silica gel column (dichloromethane˜dichloromethane:methanol=100:3)
  10. dissolutionThe purified product was dissolved in saturated ethanol hydrochloride (1 ml)
  11. concentrationfollowed by concentration under reduced pressure
  12. washwashed in ethyl acetate

出典と根拠

ORDレコード
ord-52c27a54338b400f9321c8cdab5c9048
出典データセット
uspto-grants-2003_02
特許番号
US06525042B1

反応ノート

読み込み中…