P,P-Diphenylphosphinic azide → HCID 11829615, compound

HRID 2104254Notes

Reaction equation

HRID 2104254 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:18][O:19][C:20](=[O:29])[C@:21]([CH3:28])([CH2:23][S:24]C(=O)C)[NH2:22]>>[CH3:18][O:19][C:20](=[O:29])[C@:21]([CH3:28])([CH2:23][SH:24])[NH2:22]

Participants

3

Reactant 2

HCID 199401P,P-Diphenylphosphinic azideHCID 86591052HCID 86591052, compound

Product 1

HCID 11829615HCID 11829615, compound

Procedure

Methyl t-butyl 2-methylidenyl-1,3-dipropionate is reacted with thioacetic acid to form methyl t-butyl 2-acetylthiomethyl-1,3-dipropionate. Methyl t-butyl 2-acetylthiomethyl-1,3-dipropionate is alkylated with potassium carbonate and methyl iodide in the presence of a phase transfer catalyst to form methyl t-butyl 2-acetylthiomethyl-2-methyl-1,3-dipropionate. The t-butyl group is hydrolyzed by acidifying the reaction mixture. The free carboxylic acid group produced by hydrolyzing the t-butyl group is converted to an amino group through a reaction with diphenylphosphoryl azide, thereby forming S-acetyl-2-methylcysteine methyl ester. The acetyl group is removed to form 2-methylcysteine methyl ester.

Workup

  1. customThe free carboxylic acid group produced
  2. customThe acetyl group is removed

Sources & evidence

ORD record
ord-dd9dc215a97e404aac0da5dae181c716
Source dataset
uspto-grants-2009_08
Patent number
US07576234B2

Reaction notes

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