Hydrochloric Acid → HCID 70186181, compound

HRID 963737Notes

Reaction equation

HRID 963737 reaction equation
C[O:2][C:3]([CH2:5][O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH:11]([CH2:17][NH:18][C:19](=[O:34])[O:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:12]2)=[O:4].CO.COCCOC.Cl>[OH-].[Na+]>[C:3]([CH2:5][O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH:11]([CH2:17][NH:18][C:19](=[O:34])[O:20][CH:21]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:12]2)([OH:4])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 80711,2-DimethoxyethaneHCID 70187837HCID 70187837, compound

Product 1

HCID 70186181HCID 70186181, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of benzhydryl N-[[1,2,3,4-tetrahydro-5-(methoxycarbonylmethoxy)-2-naphthyl]methyl]carbamate (60 mg) in a mixture of 1N sodium hydroxide aqueous solution (0.20 ml), methanol (1 ml), and 1,2-dimethoxyethane (1 ml) was stirred at room temperature for 30 minutes, neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was powdered from diisopropyl ether to afford benzhydryl N-[[1,2,3,4-tetrahydro-5-(carboxymethoxy)-2-naphthyl]methyl]carbamate (51 mg) as a colorless powder. mp: 160°-161° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-ca6f287991964fbeb5ef51a0bb34892a
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

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