1,2-Dichloroethane → Tert-butyl {2-[(2-amino-3,4-difluorophenyl)amino]-2-oxoethyl}carbamate

HRID 908244

반응식

HRID 908244 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[F:27][C:28]1[C:33]([F:34])=[CH:32][CH:31]=[C:30]([NH2:35])[C:29]=1[NH2:36].C(N(CC)C(C)C)(C)C>CN(C=O)C>[NH2:36][C:29]1[C:28]([F:27])=[C:33]([F:34])[CH:32]=[CH:31][C:30]=1[NH:35][C:10](=[O:12])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 27367533,4-Difluorobenzene-1,2-diamine

생성물 1

HCID 58024790Tert-butyl {2-[(2-amino-3,4-difluorophenyl)amino]-2-oxoethyl}carbamate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a 130 mL DMF solution of [(tert-butoxycarbonyl)amino]acetic acid (14.1 g, 80.4 mmol) were added EDC (18.8 g, 96.2 mmol), HOBt (13.1 g, 96.2 mmol), 3,4-difluoro-benzene-1,2-diamine (11.2 g, 77.7 mmol) and N,N-diisopropylethylamine (27.1 mL, 156 mmol). The reaction mixture was stirred at room temperature for 6 hr. The resulting suspension was filtered and the filtrate was diluted with EtOAc, washed with sat. ammonium chloride aq., sat. sodium bicarbonate aq. and brine, dried over anhydrous Na2SO4 filtered and concentrated to give the title compound as crude solid product (24 g). LC/MS: m/z 302(M+H).

후처리

  1. filtrationThe resulting suspension was filtered
  2. additionthe filtrate was diluted with EtOAc
  3. washwashed with sat. ammonium chloride aq., sat. sodium bicarbonate aq. and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bf3bd96ba15c4a6d82fb927871de96ef
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017605B2

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