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Carbonic acid, 1-chloroethyl ethyl ester → 1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-tetrazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-4-[1-(ethoxy-carbonyloxy)ethyl]-1H-1,2,4-triazolium chloride

HRID 2186912
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HRID 2186912 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:35])([CH2:29][N:30]1[CH:34]=[N:33][CH:32]=[N:31]1)[C@H:10]([N:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH:27]=[N:26][N:25]=[N:24]3)=[CH:19][CH:18]=2)[C:13]1=[O:28])[CH3:11].[C:36](=[O:44])([O:41][CH2:42][CH3:43])[O:37][CH:38]([Cl:40])[CH3:39]>C(#N)C>[Cl-:40].[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:35])([C@H:10]([N:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH:27]=[N:26][N:25]=[N:24]3)=[CH:19][CH:18]=2)[C:13]1=[O:28])[CH3:11])[CH2:29][NH+:30]1[CH2:34][N:33]([CH:38]([O:37][C:36]([O:41][CH2:42][CH3:43])=[O:44])[CH3:39])[CH:32]=[N:31]1
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참가 물질

4

반응물 2

HCID 162095Carbonic acid, 1-chloroethyl ethyl esterHCID 3002973Tak 456

생성물 1

HCID 699428981-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-tetrazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-4-[1-(ethoxy-carbonyloxy)ethyl]-1H-1,2,4-triazolium chloride수율 1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
95 °C

실험 절차

To a mixture of 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-tetrazol-1-yl)phenyl]-2-imidazolidinone (0.61 g) and 1-chloroethyl ethyl carbonate (3.7 g) was added acetonitrile (1 ml), and the mixture was stirred for 38 hours at 95° C. The reaction mixture was concentrated under reduced pressure. To the residue was added diisopropyl ether (10 ml), and the resulting powder was collected by filtration. The powder was subjected to ODS column chromatography (eluent: methanol/water=3/2). The eluate was concentrated in vacuo. The residue was dissolved in water (10 ml), and lyophilized to give 1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-tetrazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-4-[1-(ethoxy-carbonyloxy)ethyl]-1H-1,2,4-triazolium chloride (Compound 7,90 mg) as a white powder.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added diisopropyl ether (10 ml)
  3. filtrationthe resulting powder was collected by filtration
  4. concentrationThe eluate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in water (10 ml)

출처 및 근거

ORD 기록
ord-4eed9678220b4fac8330af905b0df617
출처 데이터셋
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06407129B1

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