3-Acetylsulfanyl-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-butyric acid ethyl ester → 2-(6-Amino-pyridin-3-ylmethyl)-3-mercapto-butyric acid

HRID 1789875Notes

Reaction equation

HRID 1789875 reaction equation
C([O:3][C:4](=[O:27])[CH:5]([CH2:12][C:13]1[CH:14]=[N:15][C:16]([NH:19]C(OC(C)(C)C)=O)=[CH:17][CH:18]=1)[CH:6]([S:8]C(=O)C)[CH3:7])C>Cl>[NH2:19][C:16]1[N:15]=[CH:14][C:13]([CH2:12][CH:5]([CH:6]([SH:8])[CH3:7])[C:4]([OH:27])=[O:3])=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 537302483-Acetylsulfanyl-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-butyric acid ethyl ester

Product 1

HCID 97945372-(6-Amino-pyridin-3-ylmethyl)-3-mercapto-butyric acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-acetylsulfanyl-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-butyric acid ethyl ester/B (55 mg; 0.14 mmol) in concentrated HCl (2 mL) was refluxed under argon for 1 hour. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to afford 39.4 mg of the title compound as the hydrochloride salt.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0294f9f994f74d49b5d1528e5d08120d
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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