Ethyl Acetate → 4-((S)-2-((S)-3-(3-(2-aminoethylcarbamoyl)phenylsulfonyl)thiazolidine-2-carbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide hydrochloride

HRID 520341Notes

Reaction equation

HRID 520341 reaction equation
C(OC([NH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH:15]=[C:16]([S:20]([N:23]2[CH2:27][CH2:26][S:25][C@H:24]2[C:28]([O:30][C@H:31]([C:42]2[CH:47]=[CH:46][C:45]([O:48][CH:49]([F:51])[F:50])=[C:44]([O:52][CH2:53][CH:54]3[CH2:56][CH2:55]3)[CH:43]=2)[CH2:32][C:33]2[C:38]([Cl:39])=[CH:37][N+:36]([O-:40])=[CH:35][C:34]=2[Cl:41])=[O:29])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1)=[O:13])=O)(C)(C)C.C(OCC)(=O)C>Cl>[ClH:39].[NH2:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH:15]=[C:16]([S:20]([N:23]2[CH2:27][CH2:26][S:25][C@H:24]2[C:28]([O:30][C@H:31]([C:42]2[CH:47]=[CH:46][C:45]([O:48][CH:49]([F:50])[F:51])=[C:44]([O:52][CH2:53][CH:54]3[CH2:56][CH2:55]3)[CH:43]=2)[CH2:32][C:33]2[C:38]([Cl:39])=[CH:37][N+:36]([O-:40])=[CH:35][C:34]=2[Cl:41])=[O:29])(=[O:21])=[O:22])[CH:17]=[CH:18][CH:19]=1)=[O:13]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 1185584624-((S)-2-((S)-3-(3-(2-(tert-Butoxycarbonylamino)ethylcarbamoyl)phenylsulfonyl)-thiazolidine-2-carbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-ethyl)-3,5-dichloropyridine 1-oxide

Product 1

HCID 1185584544-((S)-2-((S)-3-(3-(2-aminoethylcarbamoyl)phenylsulfonyl)thiazolidine-2-carbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide hydrochlorideYield 200%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-((S)-2-((S)-3-(3-(2-(tert-Butoxycarbonylamino)ethylcarbamoyl)phenylsulfonyl)-thiazolidine-2-carbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-ethyl)-3,5-dichloropyridine 1-oxide (211 mg, 0.245 mmol) was dissolved in HCl 1N in Ethyl Acetate (5 ml, 165 mmol). The reaction was stirred at room temperature for 5 hrs to achieve completion. The reaction mixture was concentrated under vacuum, and the crude product was triturated with Et2O and filtered to give the crude 4-((S)-2-((S)-3-(3-(2-aminoethylcarbamoyl)phenylsulfonyl)thiazolidine-2-carbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide hydrochloride (195 mg, 0.245 mmol, 100% yield).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe crude product was triturated with Et2O
  3. filtrationfiltered

Sources & evidence

ORD record
ord-7abe851a9de84ae38b327c3596b7cf77
Source dataset
uspto-grants-2016_05
Patent number
US09326976B2

Reaction notes

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