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Ethanol → tert-butyl [(1R)-2-(3,4-diaminophenoxy)-1-phenylethyl]carbamate

HRID 1038973
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인쇄 미리보기

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HRID 1038973 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[N+:25]([O-])=O)[O:5][CH2:6][C@H:7]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[Cl-].[NH4+].C(O)C>[Cl-].[Na+].O.[Fe].C(OCC)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[NH2:25])[O:5][CH2:6][C@H:7]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
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참가 물질

8

반응물 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 58443038tert-butyl [(1R)-2-(3-amino-4-nitrophenoxy)-1-phenylethyl]carbamate2회

생성물 1

HCID 58443062tert-butyl [(1R)-2-(3,4-diaminophenoxy)-1-phenylethyl]carbamate

시약·촉매·용매 3

HCID 23925
Iron
촉매
HCID 8857Ethyl Acetate용매
HCID 57417360Sodium chloride; water용매

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온도
80 °C

실험 절차

tert-Butyl [(1R)-2-(3-amino-4-nitrophenoxy)-1-phenylethyl]carbamate (Intermediate 5) (346 mg, 0.93 mmol) was placed in a microwave reaction vial (10-20 mL), followed by iron (259 mg, 4.63 mmol), water (4 mL), ammonium chloride (40 mg, 0.74 mmol) and finally ethanol (4 mL). The reaction vial was sealed, and set to heat at 80° C. for twenty hours. The reaction was added to a separatory funnel containing ethyl acetate (100 mL) and brine (75 mL); the phases were separated, and the organic layer was washed again with brine (75 mL). The ethyl acetate layer was then concentrated in vacuo to afford tert-butyl [(1R)-2-(3,4-diaminophenoxy)-1-phenylethyl]carbamate as an orange solid. LRMS (ESI) cale'd for (C19H26N3O3) [M+H]+, 344.2; found 344.2.

후처리

  1. customThe reaction
  2. customvial was sealed
  3. additionThe reaction was added to a separatory funnel
  4. customthe phases were separated
  5. washthe organic layer was washed again with brine (75 mL)
  6. concentrationThe ethyl acetate layer was then concentrated in vacuo

출처 및 근거

ORD 기록
ord-cb46cb6e813f4908bf1b4e03d80f82e5
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08552019B2

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