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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Tert-butoxycarbonylalanine → [(S)-1-(3-Bromo-2-cyclopropylamino-4-fluorophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester

HRID 243139
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HRID 243139 반응식
[Br:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([NH2:9])[C:3]=1[NH:10][CH:11]1[CH2:13][CH2:12]1.[C:14]([O:18][C:19]([NH:21][C@@H:22]([CH3:26])[C:23](O)=[O:24])=[O:20])([CH3:17])([CH3:16])[CH3:15].C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:14]([O:18][C:19](=[O:20])[NH:21][C@H:22]([C:23](=[O:24])[NH:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Br:1])[C:3]=1[NH:10][CH:11]1[CH2:13][CH2:12]1)[CH3:26])([CH3:15])([CH3:16])[CH3:17]
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참가 물질

6

반응물 4

HCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 681575913-Bromo-N2-cyclopropyl-4-fluorobenzene-1,2-diamine

생성물 1

HCID 68158397[(S)-1-(3-Bromo-2-cyclopropylamino-4-fluorophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester수율 81.4%

시약·촉매·용매

1
HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

A mixture of 3-bromo-N2-cyclopropyl-4-fluorobenzene-1,2-diamine (759 mg, 3.10 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (644 mg, 3.41 mmol), HOAt (464 mg, 3.41 mmol) and N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (654 mg, 3.41 mmol) in DCM (20 mL) was stirred at 0° C. for 1 h. The reaction mixture was then partitioned between DCM and a saturated solution of NaHCO3. The organic fraction was dried and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-50% EtOAc in cyclohexane) to afford the title compound (1.05 g, 81%) as a pale beige solid. LCMS (Method C): RT 3.66 min [M+H]+ 416.05

후처리

  1. customThe reaction mixture was then partitioned between DCM
  2. customThe organic fraction was dried
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-50% EtOAc in cyclohexane)

출처 및 근거

ORD 기록
ord-78ae5010312d45bd813dcf735c14ec4a
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08653089B2

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