2-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-2-methyl-propionic acid ethyl ester → 2-Acetylsulfanylmethyl-3-(6-amino-5-methyl-pyridin-3-yl)-2-methyl-propionic acid ethyl ester

HRID 1789823Notes

Reaction equation

HRID 1789823 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[C:5]([CH2:30][S:31][C:32](=[O:34])[CH3:33])([CH3:29])[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)=[C:11]([CH3:13])[CH:12]=1)[CH3:2]>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4](=[O:35])[C:5]([CH2:30][S:31][C:32](=[O:34])[CH3:33])([CH3:29])[CH2:6][C:7]1[CH:8]=[N:9][C:10]([NH2:14])=[C:11]([CH3:13])[CH:12]=1)[CH3:2]

Participants

3

Reactant 1

HCID 542605232-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-2-methyl-propionic acid ethyl ester

Product 1

HCID 572012572-Acetylsulfanylmethyl-3-(6-amino-5-methyl-pyridin-3-yl)-2-methyl-propionic acid ethyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Crude 2-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-2-methyl-propionic acid ethyl ester (1.46 g) was dissolved in TFA (5 mL) and stirred for 60 min. Concentration under reduced pressure followed by chromathography (toluene/EtOAc, 1:1→1:10→0:1) gave slightly impure 2-acetylsulfanylmethyl-3-(6-amino-5-methyl-pyridin-3-yl)-2-methyl-propionic acid ethyl ester (696 mg, 84%)

Workup

  1. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-0b8e6143433749e2944677c438c6313f
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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