Ammonia → Benzyl 2-{[2-amino-3-(aminocarbonyl)phenyl]amino}-1,1-dimethyl-2-oxoethylcarbamate

HRID 12630

반응식

HRID 12630 반응식
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:30][C:31]1[C:39]([NH2:40])=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([NH2:35])=[O:34].N>N1C=CC=CC=1.CN(C=O)C>[NH2:30][C:31]1[C:32]([C:33]([NH2:35])=[O:34])=[CH:36][CH:37]=[CH:38][C:39]=1[NH:40][C:13](=[O:15])[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:17])[CH3:16]

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanineHCID 104870292,3-Diaminobenzamide

생성물 1

HCID 68512848Benzyl 2-{[2-amino-3-(aminocarbonyl)phenyl]amino}-1,1-dimethyl-2-oxoethylcarbamate

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6228Dimethylformamide용매

반응 조건

온도
40 °C

실험 절차

2-{[(Benzyloxy)carbonyl]amino}-2-methylpropanoic acid (5.18 g, 21.83 mmol) in a mixture of pyridine (25 mL) and DMF (25 mL) was treated with 1,1′-carbonyldiimidazole (3.72 g, 22.92 mmol) and heated at 40° C. for 2 hours. 2,3-Diaminobenzamide dihydrochlolide (4.89 g, 21.83 mmol), prepared as described in WO0026192, was added and the mixture was stirred at room temperature overnight. The solvents were removed under vacuum and the residue was partitioned between ethyl acetate and diluted sodium bicarbonate aqueous solution. The formed slightly yellow solid material was collected by filtration, washed with water and ethyl acetate, and dried to give Example 1A. MS (DCI/NH3) m/z 371 (M+H)+.

후처리

  1. additionwas added
  2. customThe solvents were removed under vacuum
  3. customthe residue was partitioned between ethyl acetate and diluted sodium bicarbonate aqueous solution
  4. customThe formed slightly yellow solid material
  5. filtrationwas collected by filtration
  6. washwashed with water and ethyl acetate
  7. customdried
  8. customto give Example 1A

출처 및 근거

ORD 기록
ord-9c25fc59113f4ee5ad6fdc1b8bb23676
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728026B2

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