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

HRID 2255295ノート

反応式

HRID 2255295 の反応式
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]

参加物

6

反応物 4

HCID 79724-Methylmorpholine2 回HCID 62365Isobutyl chloroformateHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 699519434-[(4-(Aminoiminomethyl)phenyl)amino]-4-oxobutanoic acid hydrochloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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 0.45 g β-alanine ethyl ester hydrochloride was added followed by 0.6 mL of N-methyl morpholine. After 4 hr the solvent was removed under reduced pressure and the product was purified by reverse phase chromatography (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/e 335.1(M+H+).

後処理

  1. additionwas added
  2. customAfter 4 hr the solvent was removed under reduced pressure
  3. customthe product was purified by reverse phase chromatography (water/acetonitrile)

出典と根拠

ORDレコード
ord-5090b28454af4e86a0a710fc524e3f88
出典データセット
uspto-grants-1993_08
特許番号
US05239113

反応ノート

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