Hydrogen chloride-ethyl acetate → 2-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]-2-hydroxyethyl glycinate dihydrochloride

HRID 1882005Notes

Reaction equation

HRID 1882005 reaction equation
C(OC([NH:8][CH2:9][C:10]([O:12][CH2:13][CH:14]([C:16]1[CH:17]=[N:18][C:19]([C:22]2[NH:23][C:24]([CH:27]([C:35]3[CH:40]=[CH:39][C:38]([S:41]([CH:44]4[CH2:46][CH2:45]4)(=[O:43])=[O:42])=[CH:37][CH:36]=3)[CH2:28][CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[CH:25][CH:26]=2)=[CH:20][CH:21]=1)[OH:15])=[O:11])=O)(C)(C)C.C(OCC)(=O)C.[ClH:53]>C(OCC)(=O)C.C(OCC)C>[ClH:53].[ClH:53].[NH2:8][CH2:9][C:10]([O:12][CH2:13][CH:14]([C:16]1[CH:17]=[N:18][C:19]([C:22]2[NH:23][C:24]([CH:27]([C:35]3[CH:40]=[CH:39][C:38]([S:41]([CH:44]4[CH2:46][CH2:45]4)(=[O:42])=[O:43])=[CH:37][CH:36]=3)[CH2:28][CH:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)=[CH:25][CH:26]=2)=[CH:20][CH:21]=1)[OH:15])=[O:11]

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 593312182-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]-2-hydroxyethyl N-(tert-butoxycarbonyl)glycinate

Product 1

HCID 684334432-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]-2-hydroxyethyl glycinate dihydrochlorideYield 41%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]-2-hydroxyethyl N-(tert-butoxycarbonyl)glycinate (245 mg) in ethyl acetate (5 mL) was added 4M hydrogen chloride-ethyl acetate solution (210 μL), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with diethyl ether, and the resulting precipitate was collected by filtration and dried to give the title compound (44.1 mg, yield 41%) as a pale-yellow solid. MS: 554 (MH+).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-de50073758474aecbabd29448d8da464
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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