4-Methylmorpholine → HCID 68157517、化合物

HRID 242770

反応式

HRID 242770 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:16]([O:23][C:24]([NH:26][C@@H:27]([CH3:31])[C:28](O)=O)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH2:16]([O:23][C:24](=[O:25])[NH:26][C@H:27]([C:28]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[N:8]=1)[CH3:31])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 736104N-carbobenzyloxyalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68157147HCID 68157147、化合物

生成物 1

HCID 68157517HCID 68157517、化合物収率 90.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-methyl-N2-phenyl-benzene-1,2-diamine (852 mg, 4.3 mmol) in anhydrous DCM (20 mL) were added (S)-2-benzyloxycarbonylaminopropionic acid (1.44 g, 6.45 mmol), HOBt (639 mg, 4.73 mmol), 4-methylmorpholine (1.04 mL, 9.46 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.24 g, 6.45 mmol). The mixture was stirred at RT for 6.5 h and then partitioned between DCM (100 mL) and water. The organic layer was then washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was dissolved in AcOH (10 mL) and heated to 65° C. for 18 h. After cooling to RT, volatiles were removed under reduced pressure and the residue diluted with EtOAc (100 mL). The organic layer was washed with a saturated solution of NaHCO3, followed by brine, then dried (Na2SO4) and concentrated in vacuo affording [(S)-1-(7-Methyl-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid benzyl ester as brown foam (1.5 g, 90%). LCMS: RT 3.07 min [M+H]+ 386.2.

後処理

  1. custompartitioned between DCM (100 mL) and water
  2. washThe organic layer was then washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting residue was dissolved in AcOH (10 mL)
  6. temperatureheated to 65° C. for 18 h
  7. temperatureAfter cooling to RT
  8. customvolatiles were removed under reduced pressure
  9. additionthe residue diluted with EtOAc (100 mL)
  10. washThe organic layer was washed with a saturated solution of NaHCO3
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5d92de7fe1a84244b88539d299b4d77a
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

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