Trifluoroacetic acid → HCID 89668511, compound

HRID 1482370Notes

Reaction equation

HRID 1482370 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([NH:15][C:16](=[O:33])[C@@H:17]([NH:25]C(=O)OC(C)(C)C)[CH2:18][S:19][S:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[NH2:25][C@@H:17]([CH2:18][S:19][S:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:16]([NH:15][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117752740(R)-tert-butyl (1-(benzylamino)-3-(tert-butyldisulfanyl)-1-oxopropan-2-yl)carbamate

Product 1

HCID 89668511HCID 89668511, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 ml) was added to a solution of (R)-tert-butyl (1-(benzylamino)-3-(tert-butyldisulfanyl)-1-oxopropan-2-yl)carbamate (Compound tk92) (1.049 g, 2.63 mmol) in dichloromethane (9 ml), and the reaction solution was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure and then extracted with ethyl acetate/saturated sodium bicarbonate, and the organic layer was washed with brine. The organic layer was dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to afford (R)-2-amino-N-benzyl-3-(tert-butyldisulfanyl)propanamide (Compound tk93) (810 mg, 100%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate/saturated sodium bicarbonate
  3. washthe organic layer was washed with brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-54a42dbfd1a6448c89aeb215a4259d8b
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

Loading…