Hydrochloric Acid → HCID 20828716, compound

HRID 496448Notes

Reaction equation

HRID 496448 reaction equation
[N:1]1([CH2:6][C@@H:7]([O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:21](=[O:25])[CH2:20][CH2:19][CH2:18][C:17]=3[C:16]=2[CH2:26][S:27]([C:30]2[CH:39]=[CH:38][CH:37]=[CH:36][C:31]=2[C:32]([O:34]C)=[O:33])(=[O:29])=[O:28])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Li+].Cl.[Na+].[Cl-]>ClCCl.CO.O.O1CCOCC1>[N:1]1([CH2:6][C@@H:7]([O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:21](=[O:25])[CH2:20][CH2:19][CH2:18][C:17]=3[C:16]=2[CH2:26][S:27]([C:30]2[CH:39]=[CH:38][CH:37]=[CH:36][C:31]=2[C:32]([OH:34])=[O:33])(=[O:29])=[O:28])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 5234Sodium ChlorideHCID 60029884HCID 60029884, compound

Product 1

HCID 20828716HCID 20828716, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of methyl 2-{[(2-{[(1S)-2-(1H-imidazol-1-yl)-1-phenylethyl]oxy}-5-oxo-5,6,7,8-tetrahydro-1-naphthalenyl)methyl]sulfonyl}benzoate (2.47 g, 4.54 mmol), 2N lithium hydroxide (9.1 ml), p-dioxane (45 ml) and water (27 ml) was stirred at room temperature for 2 h. Water (200 ml) was added and acidified with conc HCl to pH 3 at 0° C. Aqueous NaCl (50 ml) was added and further stirred at 0° C. for 1H. The precipitate was filtered, washed with water, and dried, to give a beige solid, 1.88 g, 78% yield; mp 230° C. (from dichloromethane-MeOH). NMR spectrum was consistent with structure. Calcd. For C29H26N2O6S.H2O:

Workup

  1. stirringfurther stirred at 0° C. for 1H
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried
  5. customto give a beige solid, 1.88 g, 78% yield

Sources & evidence

ORD record
ord-c050463121c94a9188886ca34d869057
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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