Bromomethyl acetate → HCID 69942568, compound

HRID 1370621Notes

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]=[CH:26][N:25]=[N:24]3)=[CH:19][CH:18]=2)[C:13]1=[O:28])[CH3:11].[C:36]([O:39][CH2:40][Br:41])(=[O:38])[CH3:37]>C(#N)C>[Br-:41].[C:36]([O:39][CH2:40][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:18]=[CH:19][C:20]([N:23]4[CH:27]=[CH:26][N:25]=[N:24]4)=[CH:21][CH:22]=3)[C:13]2=[O:28])[CH3:11])[N:31]=[CH:32]1)(=[O:38])[CH3:37]

Participants

Conditions

Temperature: 50 °C

Procedure

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-1,2,3-triazol-1-yl)phenyl]-2-imidazolidinone (0.5 g) and acetonitrile (10 ml) was added bromomethyl acetate (0.1 ml), and the mixture was stirred for 24 hours at 50° C. The reaction mixture was purified by silica gel flush chromatography (silica gel 25 g, eluent: ethyl acetate→acetone→acetone/ethanol=10/1). The residue purified was crystallized from ethanol to give 4-acetoxymethyl-1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-1,2,3-triazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-1H-1,2,4-triazolium bromide (Compound 10, 0.135 g) as colorless crystals.

Workup

customThe reaction mixture was purified by silica gel
customflush chromatography (silica gel 25 g, eluent: ethyl acetate→acetone→acetone/ethanol=10/1)
customThe residue purified
customwas crystallized from ethanol

Sources & evidence

ORD record: ord-17e6feea34914d519e5ca3a168c8441a
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06583164B1

Reaction notes

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