Trifluoroacetic acid → 2-Acetylsulfanylmethyl-3-(6-amino-pyridin-3-yl)-butyric acid ethyl ester

HRID 1789856Notes

Reaction equation

HRID 1789856 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([O:10][C:11](=[O:34])[CH:12]([CH2:29][S:30][C:31](=[O:33])[CH3:32])[CH:13]([C:15]1[CH:16]=[N:17][C:18]([NH:21]C(OC(C)(C)C)=O)=[CH:19][CH:20]=1)[CH3:14])[CH3:9]>C(Cl)Cl>[CH2:8]([O:10][C:11](=[O:34])[CH:12]([CH2:29][S:30][C:31](=[O:33])[CH3:32])[CH:13]([C:15]1[CH:16]=[N:17][C:18]([NH2:21])=[CH:19][CH:20]=1)[CH3:14])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867601172-Acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-butyric acid ethyl ester

Product 1

HCID 867601182-Acetylsulfanylmethyl-3-(6-amino-pyridin-3-yl)-butyric acid ethyl esterYield 132.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2 mL) was added to a solution of 2-acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-butyric acid ethyl ester (178 mg, 0.449 mmol) in methylene chloride (2 mL). The mixture was stirred for 60 min and concentrated under reduced pressure. Flash chromatography (toluene/EtOAc, 1:6) gave unpure 2-acetylsulfanylmethyl-3-(6-amino-pyridin-3-yl)-butyric acid ethyl ester (176 mg, 95%). Further purification by HPLC (10→70% acetonitrile in water, 0.1% TFA) gave 2-acetylsulfanylmethyl-3-(6-amino-pyridin-3-yl)-butyric acid ethyl ester (104 mg, 56%) as the TFA salt.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ce85ab6ceb94c2baed95550c8ddf14d
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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