Dichloromethane → (s)-2-Amino-n-(2-mercapto-ethyl)-3-methyl-butyramide

Reaction equation

C(OC(=O)[NH:7][C@H:8]([C:12](=[O:17])[NH:13][CH2:14][CH2:15][SH:16])[CH:9]([CH3:11])[CH3:10])(C)(C)C.C(Cl)Cl.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[NH2:7][C@@H:8]([CH:9]([CH3:11])[CH3:10])[C:12]([NH:13][CH2:14][CH2:15][SH:16])=[O:17]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 12052Triethylsilane

HCID 87903836HCID 87903836, compound

Product 1

HCID 3078315(s)-2-Amino-n-(2-mercapto-ethyl)-3-methyl-butyramide

Procedure

To 26g (222.0 mg, 0.80 mmol) in a 100 mL round-bottom flask purged with argon were added CH2Cl2 (2.00 mL, 31.2 mmol), triethylsilane (1.28 mL, 8.0 mmol), and trifluoroacetic acid (616 μL, 8.0 mmol). The reaction was stirred for 2.5 hours at room temperature, then concentrated in vacuo. The crude product was purified by silica gel chromatography using 10% methanolic CH2Cl2 as eluant. Clean fractions were combined, and concentrated in vacuo to afford 27g as a colorless oil.