Methanol → HCID 86734237, compound

HRID 1973166Notes

Reaction equation

HRID 1973166 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].[C:10](Cl)(Cl)=[O:11].[CH3:14][OH:15].[OH-:16].[Na+]>C1(C)C=CC=CC=1>[C:14]([NH:1][C@H:2]([C:10]([OH:11])=[O:16])[CH2:3][CH2:4][S:5][CH3:6])([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6])=[O:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 6137L-MethionineHCID 6371PhosgeneHCID 14798Sodium Hydroxide

Product 1

HCID 86734237HCID 86734237, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

L-methionine in 3N NaOH is reacted with 0.5 equiv. of phosgene in toluene at about 0° with vigorous stirring. Recrystallization from 15% acetic acid of the product obtained upon acidification of the reaction mixture gives carbonyl-bis (L-methionine) in 30-40% yield, m.p. 167°-180° [α]D25 +4.8 (C, 1 methanol). The carbonyl-bis (L-methionine) is then reacted in dimethylformamide with two equiv. of dicyclohexylcarbodiimide and p-nitrophenol to yield the active ester, carbonyl-bis (L-methionine p-nitrophenyl ester) in 80% yield (after crystallization from tetrahydrofuran-ether), m.p. 183°-140°; [α]D25 = -41° (c, 0.5, dimethylformamide).

Workup

  1. customRecrystallization from 15% acetic acid of the product
  2. customobtained upon acidification of the reaction mixture

Sources & evidence

ORD record
ord-63e674a1b23a495dba2440515b678deb
Source dataset
uspto-grants-1976_12
Patent number
US03996268

Reaction notes

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