Ammonia → HCID 20285441, compound

HRID 127621Notes

Reaction equation

HRID 127621 reaction equation
N.C([S:5][CH2:6][CH:7]([CH3:22])[C:8]([N:10]([CH:15]1[CH2:21][CH2:20][CH2:19][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]([CH3:22])[C:8]([N:10]([CH:15]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:11][C:12]([OH:14])=[O:13])=[O:9]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 20285458HCID 20285458, compound

Product 1

HCID 20285441HCID 20285441, compoundYield 88%

Procedure

Ammonia gas was bubbled slowly through a stirred methanolic solution of N-(3-acetylthio-2-methylpropanoyl)-N-cycloheptyl glycine (7.2 g, 0.023 mol) for two hours. The reaction mixture was then concentrated and the residue redissolved in methylene chloride (300 ml). This solution was washed with 5% aqueous sodium bisulfate (5×200 ml), dried over MgSO4, filtered and concentrated to yield 5.5 g (88%) crude product. This material was purified further by HPLC, with ethyl acetate/toluene/hexane/acetic acid (50:25:50:2) as the eluent. Rf 0.5 (Toluene/Acetic Acid, 7:3), Rf 0.3 (Ethyl acetate/hexane, acetic acid 50;50;2).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionthe residue redissolved in methylene chloride (300 ml)
  3. washThis solution was washed with 5% aqueous sodium bisulfate (5×200 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-90335d733c8e4e37b11a9fa871a86a59
Source dataset
uspto-grants-1981_03
Patent number
US04256761

Reaction notes

Loading…