2-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-yl)-propionic acid ethyl ester → 3-(6Amino-4-methyl-pyridin-3-yl)-2-mercaptomethyl-propionic acid

HRID 1789841Notes

Reaction equation

HRID 1789841 reaction equation
C([O:3][C:4](=[O:34])[CH:5]([CH2:29][S:30]C(=O)C)[CH2:6][C:7]1[CH:8]=[N:9][C:10]([N:14](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[CH:11][C:12]=1[CH3:13])C>Cl>[NH2:14][C:10]1[N:9]=[CH:8][C:7]([CH2:6][CH:5]([CH2:29][SH:30])[C:4]([OH:34])=[O:3])=[C:12]([CH3:13])[CH:11]=1

Participants

3

Reactant 1

HCID 570945672-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-yl)-propionic acid ethyl ester

Product 1

HCID 97945363-(6Amino-4-methyl-pyridin-3-yl)-2-mercaptomethyl-propionic acidYield 114.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-Acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-yl)-propionic acid ethyl ester (36 mg, 0.072 mmol) was dissolved in conc. HCl (3.0 mL). The solution was heated to reflux for 1 h. Concentration under reduced pressure gave the title compound (18.7 mg, 98%) as the hydrochloride salt.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 h
  3. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-d41aba1fce454adcb3f51d2dde176afd
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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