Ethylene → Valine methyl ester

HRID 1763265Notes

Reaction equation

HRID 1763265 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C@H:4]([CH:12]([CH3:14])[CH3:13])[NH:5]C(OCCBr)=O.C=C>CO.[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>[CH3:1][O:2][C:3](=[O:15])[C@H:4]([CH:12]([CH3:14])[CH3:13])[NH2:5]

Participants

5

Reactant 2

HCID 6325EthyleneHCID 53741726HCID 53741726, compound

Product 1

HCID 94285Valine methyl esterYield 76.2%

Reagents, catalysts & solvents 2

HCID 136397885HCID 136397885, compoundCatalystHCID 887MethanolSolvent

Procedure

7.7 g (8.5 mmols) of lithium cobalt-phthalocyanine in 50 ml of methanol are stirred with 846 mg (3.0 mmols) of 2-bromoethoxycarbonyl-L-valine methyl ester for 2 hours at 20° C (end of the evolution of ethylene) and the mixture is worked up as described in Example 56. 300 mg (76%) of L-valine methyl ester are obtained. Boiling point10 = 53° C. [α]D25 = +42.2° (c = 0.7 in ethanol).

Sources & evidence

ORD record
ord-0b139c823217452e846a9dfb50ca23ae
Source dataset
uspto-grants-1978_09
Patent number
US04111933

Reaction notes

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