Carbon Dioxide → tert-Butyl L-valinate

HRID 1763266Notes

Reaction equation

HRID 1763266 reaction equation
C1(O)C=CC=CC=1.[C:8]([O:12][C:13](=[O:27])[C@H:14]([CH:24]([CH3:26])[CH3:25])[NH:15]C(OCC(Cl)(Cl)Cl)=O)([CH3:11])([CH3:10])[CH3:9].O.C(=O)=O>CC(C)=O.[Co].[Li].C1C=CC2C(=C3N=C4N=C(C5C=CC=CC=54)N=C4NC(C5C=CC=CC=54)=NC4=NC(C5C=CC=CC=54)=NC=2N3)C=1>[C:8]([O:12][C:13](=[O:27])[C@H:14]([CH:24]([CH3:25])[CH3:26])[NH2:15])([CH3:11])([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 280Carbon Dioxide2×HCID 962WaterHCID 996PhenolHCID 54218914HCID 54218914, compound

Product 1

HCID 114626tert-Butyl L-valinateYield 75%

Reagents, catalysts & solvents 2

HCID 136397885HCID 136397885, compoundCatalystHCID 180AcetoneSolvent

Procedure

5.4 g (6.0 mmols) of lithium -cobalt-phthalocyanine in 30 ml of absolute acetone, 1 g (about 10 mmols) of phenol and 700 mg (2.0 mmols) of 2,2,2-trichloroethoxycarbonyl-L-valine tert.-butyl ester are stirred for 1 hour at 20° C. 10 ml of water saturated with CO2 are added to the deep green solution, CO2 and air are passed into the mixture for 5 minutes and the mixture is left to stand for 30 minutes. Cobalt phthalocyanine is filtered off and rinsed with water and acetone, the acetone is stripped off from the filtrate and the residual aqueous phase is extracted with CH2Cl2. Stripping of the combined CH2Cl2 extracts (after drying over Na2SO4) gives L-valine tert.-butyl ester which is contaminated with traces of PcC and contains diacetone alcohol. Purification via the hydrocitrate gives 260 mg (75% yield).

Workup

  1. waitthe mixture is left
  2. waitto stand for 30 minutes
  3. filtrationCobalt phthalocyanine is filtered off
  4. washrinsed with water and acetone
  5. extractionthe residual aqueous phase is extracted with CH2Cl2
  6. dry with material(after drying over Na2SO4)

Sources & evidence

ORD record
ord-c4ebc91915744758957131ef4cb8042d
Source dataset
uspto-grants-1978_09
Patent number
US04111933

Reaction notes

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