Hydrogen chloride-ethyl acetate → HCID 9875138, compound

HRID 379654Notes

Reaction equation

HRID 379654 reaction equation
[Br-:1].C(O[C:7]([N:9]([CH2:11][C:12]([O:14][C:15]1[C:52]([CH3:53])=[CH:51][C:18]([CH2:19][N+:20]2[CH:21]=[N:22][N:23]([CH2:25][C@@:26]([C:43]3[CH:48]=[C:47]([F:49])[CH:46]=[CH:45][C:44]=3[F:50])([OH:42])[C@H:27]([C:29]3[S:30][CH:31]=[C:32]([C:34]4[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=4)[N:33]=3)[CH3:28])[CH:24]=2)=[CH:17][C:16]=1[CH3:54])=[O:13])C)=O)(C)(C)C.C(OC(=O)C)C.Cl>C(OC(=O)C)C>[Br-:1].[C:40]([C:37]1[CH:36]=[CH:35][C:34]([C:32]2[N:33]=[C:29]([C@H:27]([CH3:28])[C@:26]([C:43]3[CH:48]=[C:47]([F:49])[CH:46]=[CH:45][C:44]=3[F:50])([OH:42])[CH2:25][N:23]3[CH:24]=[N+:20]([CH2:19][C:18]4[CH:17]=[C:16]([CH3:54])[C:15]([O:14][C:12](=[O:13])[CH2:11][NH:9][CH3:7])=[C:52]([CH3:53])[CH:51]=4)[CH:21]=[N:22]3)[S:30][CH:31]=2)=[CH:39][CH:38]=1)#[N:41]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 70113440HCID 70113440, compound

Product 1

HCID 9875138HCID 9875138, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 36 mg of 4-{4-[(tert-Butoxycarbonyl-methyl-amino)-acetoxy]-3,5-dimethyl-benzyl}-1-[(2R,3R)-3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium bromide in ethylacetate(2 ml) was added dropwise 4N HCl ethylacetate solution(1 mL) and the mixture was stirred at r.t. for 4 hrs. The precipitate was filtered and washed with diethylether to give 1-{(2R,3R) -3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl}-4-(3,5-dimethyl-4-methylaminoacetoxy-benzyl)-1H-[1,2,4]triazol-4-ium bromide (24.5 mg, 74% as HCl salt and as white solid);

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with diethylether

Sources & evidence

ORD record
ord-ee18f4aef01d400f94a09c15bb25c8da
Source dataset
uspto-grants-2001_10
Patent number
US06300353B1

Reaction notes

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