4-Methylmorpholine → Ethyl-3-[[4-[[4-(aminoimino-methyl)phenyl]amino]-1,4-dioxobutyl]amino]propanoate

HRID 1741189

반응식

HRID 1741189 반응식
Cl.[NH2:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:7][CH:6]=1.CN1CCOCC1.ClC(OCC(C)C)=O.Cl.[CH2:35]([O:37][C:38](=[O:42])[CH2:39][CH2:40][NH2:41])[CH3:36]>CN(C=O)C>[CH2:35]([O:37][C:38](=[O:42])[CH2:39][CH2:40][NH:41][C:15](=[O:17])[CH2:14][CH2:13][C:12]([NH:11][C:8]1[CH:7]=[CH:6][C:5]([CH:4]=[N:3][NH2:2])=[CH:10][CH:9]=1)=[O:18])[CH3:36]

참가 물질

6

반응물 4

HCID 79724-Methylmorpholine2회HCID 62365Isobutyl chloroformateHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 699519434-[(4-(Aminoiminomethyl)phenyl)amino]-4-oxobutanoic acid hydrochloride

생성물 1

HCID 70063547Ethyl-3-[[4-[[4-(aminoimino-methyl)phenyl]amino]-1,4-dioxobutyl]amino]propanoate수율 449.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

An aliquot of 4-[[4-(aminoiminomethyl)phenyl]-amino]-4-oxobutanoic acid hydrochloride prepared in Example 1, Step 1 (1.36 g) was added to dry DMF (50 ml) followed by N-methylmorpholine (0.6 mL) and isobutyl chloroformate (0.65 mL) at 0° C. under nitrogen atmosphere. The mixture was stirred for 5 min, then 0.45 g β-alanine ethyl ester hydrochloride was added followed by 0.6 mL of N-methylmorpholine. After 4 hr, the solvent was removed under reduced pressure and the product was purified by reverse phase chromatography (0.05% TFA water/acetonitrile) to give 4.4 g of white solid: 1H NMR (d6 -DMSO) δ 1.2 (t, 3H, J=7 Hz), 2.45 (m, 4H), 2.6 (m, 2H), 3.25 (m, 2H), 4.05 (q, 2H, J=7 Hz), 7.8 (s, 4H), 8.0 (m, 1H), 8.85 (bs, 2H), 9.18 (bs, 2H), 10.4 (s, 1H); MS (ES) m/z 335.1 (MH+).

후처리

  1. waitAfter 4 hr
  2. customthe solvent was removed under reduced pressure
  3. customthe product was purified by reverse phase chromatography (0.05% TFA water/acetonitrile)

출처 및 근거

ORD 기록
ord-1de35a68b4344d83b74db4bbe1a60dc2
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05973003

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