Ethyl chloroformate → HCID 22710460, 화합물

HRID 1061077노트

반응식

HRID 1061077 반응식
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

참가 물질

8

반응물 4

HCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 11272253HCID 11272253, 화합물HCID 15620607Glyoxylic acid, monohydrate

생성물 1

HCID 22710460HCID 22710460, 화합물수율 72.6%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-52c27a54338b400f9321c8cdab5c9048
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525042B1

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