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Hydrochloric Acid → 5-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1881869
Notes
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Reaction equation

HRID 1881869 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[C:14](=[O:32])[CH2:15][CH2:16][C:17]([C:19]3[S:20][C:21]([CH2:24][O:25]C4CCCCO4)=[CH:22][N:23]=3)=[O:18])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([CH2:33][CH:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)[C:14](=[O:32])[CH2:15][CH2:16][C:17]([C:19]3[S:20][C:21]([CH2:24][OH:25])=[CH:22][N:23]=3)=[O:18])=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59331382HCID 59331382, compound

Product 1

HCID 593312225-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dioneYield 73%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A mixture of 5-[4-(cyclopropylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)-1-{5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazol-2-yl}hexane-1,4-dione (3.35 g), 1M hydrochloric acid (6 mL) and tetrahydrofuran (10 mL) was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (1.83 g, yield 73%) was obtained as a colorless oil from a fraction eluted with ethyl acetate. MS: 492 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-07491b25905a47d198365d7f30c5a17e
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318746B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes