Ammonia → N-(3-Mercapto-2-methylpropanoyl)-N-cyclobutylglycine

HRID 127617Notes

Reaction equation

HRID 127617 reaction equation
N.C([S:5][CH2:6][CH:7]([CH3:19])[C:8]([N:10]([CH:15]1[CH2:18][CH2:17][CH2:16]1)[CH2:11][C:12]([OH:14])=[O:13])=[O:9])(=O)C>>[SH:5][CH2:6][CH:7]([CH3:19])[C:8]([N:10]([CH:15]1[CH2:18][CH2:17][CH2:16]1)[CH2:11][C:12]([OH:14])=[O:13])=[O:9]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 20285450N-(3-Acetylthio-2-methylpropanoyl)-N-cyclobutylglycine

Product 1

HCID 20285470N-(3-Mercapto-2-methylpropanoyl)-N-cyclobutylglycineYield 91.5%

Procedure

Ammonia gas was bubbled through a stirred methanolic solution of N-(3-acetylthio-2-methylpropanoyl)-N-cyclobutylglycine (14.1 g, 0.052 mol) for 1 hour. This reaction mixture was left stirring 1 more hour at room temperature. Concentration on a rotary evaporator removed the remaining ammonia and most of the solvent. The residue was rediluted with methanol (500 ml) and the resultant solution was stirred with Bio-Rad AG-50W-X2 cation exchange resin (200 ml) for 1 hour. Filtration followed by concentration of the filtrate yielded 11 g (91%) of a thick yellow oil. This material was purified by HPLC with ethyl acetate, toluene, hexane, acetic acid (25:15:25:1) as the eluent to afford 8.8 g of the compound as a very viscous colorless oil.

Workup

  1. waitThis reaction mixture was left
  2. concentrationConcentration
  3. customon a rotary evaporator
  4. customremoved the remaining ammonia
  5. additionThe residue was rediluted with methanol (500 ml)
  6. stirringthe resultant solution was stirred with Bio-Rad AG-50W-X2 cation exchange resin (200 ml) for 1 hour
  7. filtrationFiltration

Sources & evidence

ORD record
ord-56c03bee92bc4172a91e1f8d6980d03c
Source dataset
uspto-grants-1981_03
Patent number
US04256761

Reaction notes

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