Hydrochloric Acid → HCID 67028844, compound

HRID 2040014Notes

Reaction equation

HRID 2040014 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C@@H:11]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:12]([O:14]C)=[O:13])=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[OH-].[Li+].Cl>O1CCOCC1.O>[CH2:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C@@H:11]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:12]([OH:14])=[O:13])=[CH:8][CH:9]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67028712HCID 67028712, compound

Product 1

HCID 67028844HCID 67028844, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of 2.03 g (6.36 mmol) of methyl (R)-3-(4-allylphenyl)-2-tert-butoxycarbonylaminopropionate (prepared as in Synlett, 2005, 12, 1877-1880) in 20 ml of dioxane/water (1:1, v/v) and 0.30 g (12.71 mmol) of lithium hydroxide was stirred at RT for 2 h and then neutralized with 1N hydrochloric acid. The reaction mixture was extracted with ethyl acetate, and the organic phase was dried over Na2SO4, filtered and concentrated. 1.90 g of the title compound were obtained.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a19bc803592842a18063bf137794bee2
Source dataset
uspto-grants-2013_11
Patent number
US08580777B2

Reaction notes

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