Hydrochloric Acid → HCID 13217295, compound

HRID 67693Notes

Reaction equation

HRID 67693 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH:18]=1)=[CH2:16])[C:10]([O:12]CC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>C(COC)OC.O>[C:1]([O:5][C:6]([NH:8][CH:9]([C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH:18]=1)=[CH2:16])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 13043919HCID 13043919, compound

Product 1

HCID 13217295HCID 13217295, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of ethyl 2-(tert-butoxycarbonylamino)-3-(3'-tetrahydropyranyloxyphenyl)-3-butenoate (0.40 g) in dimethoxyethane (10 ml) and water (2 ml) is treated with solid lithium hydroxide monohydrate (0.02 g). After stirring for 2 hours at room temperature, the mixture is diluted with water and acidified with 0.1 N hydrochloric acid to ca pH 4. Extraction with ether gives essentially pure racemic 2-(tert-butoxycarbonylamino)-3-(3'-tetrahydropyranyloxyphenyl)-3-butenoic acid (0.25 g): colorless solid.

Workup

  1. extractionExtraction with ether

Sources & evidence

ORD record
ord-84117b363a714b6cae9fa8165f712387
Source dataset
uspto-grants-1982_08
Patent number
US04346110

Reaction notes

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