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

HRID 127628

반응식

HRID 127628 반응식
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]

참가 물질

3

반응물 2

HCID 222AmmoniaHCID 13599174N-[3-(Acetylthio)-2-methyl-1-oxopropyl]-N-cyclopentylglycine

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bc4319075bf84311bd792e40cb34cf72
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04256761

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