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Ethyl Acetate → (3S)-2-Oxo-3-tert-butoxycarbonylamino-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester

HRID 363869
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HRID 363869 반응식
Cl.CN(C)CCCN=C=NCC.[C:13]([O:17][C:18]([NH:20][C@@H:21]([CH2:25][NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH2:33])[C:22]([OH:24])=O)=[O:19])([CH3:16])([CH3:15])[CH3:14].C[CH2:35][O:36][C:37]([CH3:39])=[O:38]>CN(C=O)C>[CH3:35][O:36][C:37](=[O:38])[CH2:39][N:33]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[NH:26][CH2:25][C@H:21]([NH:20][C:18]([O:17][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:19])[C:22]1=[O:24]
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참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22881946(S)-3-((2-Aminophenyl)amino)-2-((tert-butoxycarbonyl)amino)propanoic acid

생성물 1

HCID 54305289(3S)-2-Oxo-3-tert-butoxycarbonylamino-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester수율 71%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

(3S)-2-Oxo-3-tert-Butoxycarbonylamino-1,3,4,5-tetrahydro-1H-1,5-benzodiazepine. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (8.54 g, 44.5 mmol) was added to a cooled (0° C.) solution of (2S)-2-tert-butoxycarbonylamino-3-(2-aminophenylamino)propionic acid (11.95 g, 40.5 mmol) in 100 ml of DMF and stirred for 18 h. The reaction was poured into 700 ml of EtOAc and washed four times with 100 ml of H2O. The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated to give a brown solid that was purified by flash chromatography eluting with 3:7 EtOAc/hexane to give 8 g (71%) of the title compound: 1H NMR (CDCl3) δ 7.78 (1H, s), 7.02-6.95 (1H, m), 6.88-6.82 (1H, m), 6.82-6.78 (1H, m), 6.75-6.70 (1H, m), 5.8-5.7 (1H, d), 4.55-4.45 (1H, m), 3.95 (1H, s), 3.9-3.82 (1H, m), 3.48-3.40 (1H,m), 1.45 (9H,s).

후처리

  1. washwashed four times with 100 ml of H2O
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customto give a brown solid that
  6. customwas purified by flash chromatography
  7. washeluting with 3:7 EtOAc/hexane

출처 및 근거

ORD 기록
ord-2422f374cade4f5490a1159fdf44ee13
출처 데이터셋
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05874424

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