Hydrochloric Acid → n-((5s)-3-(4-(2s-(Pyrimidin-2-yl)thiomethyl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide

HRID 395567노트

반응식

HRID 395567 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[S:7][CH2:8][CH:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])=[CH:16][CH:15]=2)[CH2:11][N:10]1C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.CC(C)=O.Cl>CC(C)=O.O>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[S:7][CH2:8][CH:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])=[CH:16][CH:15]=2)[CH2:11][NH:10]1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 19044839Acetone hydrogen chlorideHCID 69997770n-((5s)-3-(4-(2s-(Pyrimidin-2-yl)thiomethyl-1-trityl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide

생성물 1

HCID 69998857n-((5s)-3-(4-(2s-(Pyrimidin-2-yl)thiomethyl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide수율 92%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

The N-trityl compound (Example 30, 0.528 g, 0.79 mM) in acetone (8 ml) at 0° C. was treated with freshly prepared HCl/acetone (4 ml) and stirred. The mixture was periodically treated with 10% HCl in water until TLC indicated consumption of starting material. The reaction mixture was then diluted with EtOAc (30 ml) and taken to pH 11 with NH4OH solution. The aqueous layer was extracted with EtOAc and the combined organics dried (MgSO4) and evaporated to a residue which was triturated with diethyl ether to give the title amine (0.309 g, 92%) which was used without further purification.

후처리

  1. customconsumption of starting material
  2. additionThe reaction mixture was then diluted with EtOAc (30 ml)
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organics dried (MgSO4)
  5. customevaporated to a residue which
  6. customwas triturated with diethyl ether

출처 및 근거

ORD 기록
ord-0030985c8ff84c79b30fcf1ac4e763f2
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06605630B1

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