Iodine → tert-Butyl 4-amino-3-iodobenzylcarbamate

HRID 966532노트

반응식

HRID 966532 반응식
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Ca+2].[I:22]I>CO>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[C:13]([I:22])[CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 807IodineHCID 10112Calcium CarbonateHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamate

생성물 1

HCID 10383091tert-Butyl 4-amino-3-iodobenzylcarbamate수율 47%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a mixture of (4-amino-benzyl)-carbamic acid tert-butyl ester (4.8 g, 21.6 mmol) and calcium carbonate (2.7 g, 27 mmol) in methanol (60 mL) was added iodine (5.5 g, 21.6 mmol) in portions. The mixture was heated at reflux overnight and then concentrated in vacuo to give a dark brown residue, which was partitioned between ethyl acetate and saturated sodium bisulfite solution. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give a residue, which was purified by chromatography (5%-20% ethyl acetate in hexanes) to give 3.5 g (47%) of the desired product as a brown semi-solid. MS(APCI+): m/z 349.1 (MH+).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated in vacuo
  4. customto give a dark brown residue, which
  5. customwas partitioned between ethyl acetate and saturated sodium bisulfite solution
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo
  10. customto give a residue, which
  11. customwas purified by chromatography (5%-20% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-0e25684666ea4fcb97dd193a43e2935f
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951848B2

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