181869-54-5 → HCID 69943172, compound

HRID 1370632Notes

Reaction equation

HRID 1370632 reaction equation
[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:54])([O:51][CH2:52][I:53])[O:37][CH2:38][CH2:39][CH2:40][C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42]>C(#N)C>[I-:53].[CH2:44]([O:43][C:41]([CH2:40][CH2:39][CH2:38][O:37][C:36]([O:51][CH2:52][N:33]1[CH2:34][NH+:30]([CH2:29][C@@:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])([OH:35])[C@H:10]([N:12]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]=[N:26][N:25]=[N:24]4)=[CH:19][CH:18]=3)[C:13]2=[O:28])[CH3:11])[N:31]=[CH:32]1)=[O:54])=[O:42])[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

4

Reactant 2

HCID 3002973181869-54-5HCID 12019892HCID 12019892, compound

Product 1

HCID 69943172HCID 69943172, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution 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 (1.0 g) in acetonitrile (15 ml) was added (3-benzyloxycarbonylpropyl) iodomethyl carbonate (1.0 g) under a nitrogen atmosphere, and the mixture was stirred for 20 hours at 45-50 C. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: ethyl acetate→acetone ), and a fraction containing the desired compound was concentrated under reduced pressure. The residue was subjected to ODS column chromatography (eluent: methanol/water=3/2) to give 4-[(3-benzyloxycarbonylpropoxy)carbonyloxymethyl]-1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-tetrazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-1H-1,2,4-triazolium iodide (Compound 32, 1.47 g) as a yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona fraction containing the desired compound
  3. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-803371d473464747ac128ffd72a5ed95
Source dataset
uspto-grants-2003_06
Patent number
US06583164B1

Reaction notes

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