Ammonia → (S)-[Cyclopentyl-(3-mercapto-2-methyl-propionyl)-amino]-acetic acid

HRID 127628

Reaction equation

HRID 127628 reaction equation
N.C([S:5][CH2:6][CH:7]([CH3:20])[C:8]([N:10]([CH:15]1[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]([CH3:20])[C:8]([N:10]([CH:15]1[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 13599174N-[3-(Acetylthio)-2-methyl-1-oxopropyl]-N-cyclopentylglycine

Product 1

HCID 13469595(S)-[Cyclopentyl-(3-mercapto-2-methyl-propionyl)-amino]-acetic acid

Procedure

Ammonia gas was bubbled through a methanolic solution of N-(3-acetylthio-2-methylpropanoyl)-N-cyclopentylglycine (10.4 g, 0.036 mol) for one hour. The reaction mixture was then stoppered and stirred for 30 more minutes and then concentrated. The residue was redissolved in ethyl acetate (400 ml) and was washed with 5% aqueous sodium bisulfate (3×150 ml). The organic portion was then removed, dried (MgSO4), filtered and concentrated. The crude material was further purified by HPLC with ethyl acetate, toluene, hexane, acetic acid (50:25:50:2) as the eluent. The desired product was isolated as a nearly colorelss oil (pale yellowish tinge). 7.9 g (90%) was so obtained.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was redissolved in ethyl acetate (400 ml)
  3. washwas washed with 5% aqueous sodium bisulfate (3×150 ml)
  4. customThe organic portion was then removed
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was further purified by HPLC with ethyl acetate, toluene, hexane, acetic acid (50:25:50:2) as the eluent

Sources & evidence

ORD record
ord-bc4319075bf84311bd792e40cb34cf72
Source dataset
uspto-grants-1981_03
Patent number
US04256761

Linked notes

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