Methanol → 4-((4-bromo-1-trityl-1H-imidazol-2-yl)(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methylamino)-N'-acetoxybenzamidine

HRID 2104972Notes

Reaction equation

HRID 2104972 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([N:26]([CH2:37][C:38]2[CH:43]=[C:42]([O:44][CH2:45][CH3:46])[CH:41]=[C:40]([O:47][CH:48]([CH3:50])[CH3:49])[C:39]=2[F:51])[C:27]2[CH:36]=[CH:35][C:30]([C:31]([NH2:34])=[N:32][OH:33])=[CH:29][CH:28]=2)[N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.[CH3:52][C:53](OC(C)=O)=[O:54].CO>CCOC(C)=O>[Br:1][C:2]1[N:3]=[C:4]([N:26]([CH2:37][C:38]2[CH:43]=[C:42]([O:44][CH2:45][CH3:46])[CH:41]=[C:40]([O:47][CH:48]([CH3:50])[CH3:49])[C:39]=2[F:51])[C:27]2[CH:36]=[CH:35][C:30]([C:31]([NH2:34])=[N:32][O:33][C:53](=[O:54])[CH3:52])=[CH:29][CH:28]=2)[N:5]([C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 866079354-((4-bromo-1-trityl-1H-imidazol-2-yl)(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methylamino)-N'-hydroxybenzamidine

Product 1

HCID 867609384-((4-bromo-1-trityl-1H-imidazol-2-yl)(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methylamino)-N'-acetoxybenzamidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of Intermediate 66.1 in 20 mL EtOAc, was added 0.5 mL Ac2O. The reaction mixture was stirred at rt for 1 h, then was treated with 1 mL MeOH and evaporated to afford Intermediate 66.2, which was used in the following step without further purification.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-ad36a6a4218e4c0ca9f1fb1149359bab
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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