Hydrochloric Acid → HCID 10601170, compound

HRID 1645789Notes

Reaction equation

HRID 1645789 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:8]([CH:10]([CH2:17][S:18]([C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)(=[O:20])=[O:19])[CH2:11][CH2:12][C:13]([O:15]C)=[O:14])=[O:9])=[O:5])[CH3:2].C[S-].[Li+].Cl>CN(C)P(=O)(N(C)C)N(C)C>[CH2:1]([O:3][C:4]([CH2:6][N:7]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:8]([CH:10]([CH2:17][S:18]([C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)(=[O:20])=[O:19])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:9])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11018798HCID 11018798, compoundHCID 19802327HCID 19802327, compound

Product 1

HCID 10601170HCID 10601170, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

To a solution of methyl 4-(N-ethoxycarbonylmethyl-N-pentylcarbamoyl)-5-(2-naphthylsulfonyl)pentanoate (50 mg) in dry hexamethylphosphoric triamide (0.3 ml) was added lithium thiomethoxide (5 mg) under argon. After stirring at room temperature for 30 minutes, a dilute hydrochloric acid was added, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over MgSO4, and evaporated at reduced pressure. The residue was purified by medium pressure liquid column chromatography on silica eluting with chloroform/methanol (9:1), and recrystallized from isopropyl ether-hexane to give 23 mg of 4-(N-ethoxycarbonylmethyl-N-pentylcarbamoyl)-5-(2-naphthylsulfonyl)pentanoic acid. The physical properties of this compound were identical to that of compound No. 19, which was prepared in example 7.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated at reduced pressure
  5. customThe residue was purified by medium pressure liquid column chromatography on silica eluting with chloroform/methanol (9:1)
  6. customrecrystallized from isopropyl ether-hexane

Sources & evidence

ORD record
ord-c7975ac72bd5485d96444e324184d5db
Source dataset
uspto-grants-1993_01
Patent number
US05177069

Reaction notes

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