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

HRID 908244

反応式

HRID 908244 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bf3bd96ba15c4a6d82fb927871de96ef
出典データセット
uspto-grants-2011_09
特許番号
US08017605B2

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