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

HRID 1824689Notes

Reaction equation

HRID 1824689 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

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 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.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product was purified by silica gel chromatography
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c0abe223325448de87a4995e6244ac11
Source dataset
uspto-grants-2006_05
Patent number
US07045360B2

Reaction notes

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