Chlorotrimethylsilane → HCID 22323650, 화합물

HRID 1872338노트

반응식

HRID 1872338 반응식
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][OH:8].C[Si](Cl)(C)C.[C:14]1([C:20]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[S:21]Cl)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1.C(Cl)Cl>[OH:1][CH2:2][CH2:3][N:4]([S:21][C:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:5][CH2:6][CH2:7][OH:8]

참가 물질

6

반응물 3

HCID 6397ChlorotrimethylsilaneHCID 342378Triphenylmethanesulfenyl ChlorideHCID 30150593-((2-Hydroxyethyl)amino)propanol

생성물 1

HCID 22323650HCID 22323650, 화합물

시약·촉매·용매 2

HCID 1049Pyridine용매2회HCID 6344Dichloromethane용매

실험 절차

N-(2-hydroxyethyl)-3-amino-1-propanol (5.0 g, 41.9 mmol) is coevaporated several times with pyridine (20 mL) and then dissolved in pyridine (100 mL). The reaction flask is flushed with Argon and trimethylsilylchloride (2.47 g, 209.5 mmol) is added dropwise. The reaction mixture is stirred for 1 hour. Triphenyl methanesulfenyl chloride (14.32 g, 46.09 mmol) is dissolved in CH2Cl2 and added via dropping funnel to the cooled reaction mixture. The reaction mixture is warmed to room temperature and stirred for 18 hours. The reaction mixture is concentrated in vacuo and the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1). The H2O layer is separated and extracted with EtOAc (3×50 ml). The EtOAc extracts are pooled, dried (MgSO4) and filtered. The filtrate is concentrated in vacuo and the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound.

후처리

  1. additionis added dropwise
  2. additionadded
  3. customto the cooled reaction mixture
  4. stirringstirred for 18 hours
  5. concentrationThe reaction mixture is concentrated in vacuo
  6. customthe resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1)
  7. customThe H2O layer is separated
  8. extractionextracted with EtOAc (3×50 ml)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationThe filtrate is concentrated in vacuo
  12. customthe residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent
  13. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b5bb93f8bf0446fe8b676944fe36c149
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06107482

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