4-Methylmorpholine → HCID 68158134, 화합물

HRID 242776노트

반응식

HRID 242776 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]=1[NH2:15].[C:16]([O:20][C:21]([NH:23][C@@H:24]([CH3:28])[C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:16]([O:20][C:21](=[O:22])[NH:23][C@H:24]([C:25](=[O:26])[NH:15][C:3]1[C:4]([NH:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[CH3:28])([CH3:17])([CH3:18])[CH3:19]

참가 물질

7

반응물 5

HCID 79724-Methylmorpholine2회HCID 757711-Hydroxybenzotriazole2회HCID 85082Tert-butoxycarbonylalanine3회HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride3회HCID 534243143-Methyl-N1-phenylbenzene-1,2-diamine

생성물 1

HCID 68158134HCID 68158134, 화합물수율 56%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-methyl-N1-phenylbenzene-1,2-diamine (381 mg, 1.92 mmol) in anhydrous DCM (10 mL) were added (S)-2-tertbutoxycarbonylaminopropionic acid (399 mg, 2.11 mmol), HOBt (285 mg, 2.11 mmol), 4-methylmorpholine (464 μL, 4.22 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (405 mg, 2.11 mmol). The mixture was stirred at RT for 2 h then additional amounts of (S)-2-tertbutoxycarbonylaminopropionic acid (145 mg, 0.77 mmol) and of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (148 mg, 0.77 mmol) were added. Stirring was continued for 18 h and then additional amounts of (S)-2-tertbutoxycarbonylaminopropionic acid (545 mg, 2.88 mmol), HOBt (285 mg, 2.11 mmol), 4-methylmorpholine (464 μL, 4.22 mmol) and of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (553 mg, 2.88 mmol) were added. Stirring was continued for 24 h and then the crude mixture was purified by column chromatography (Si—PCC, gradient 0-40% EtOAc in cyclohexane) affording [(S)-1-(2-methyl-6-phenylaminophenylcarbamoyl)ethyl]carbamic acid tertbutyl ester as an orange oil (395 mg, 56%). LCMS: RT 3.69 min [M+H]+ 370.2.

후처리

  1. stirringStirring
  2. waitwas continued for 18 h
  3. stirringStirring
  4. waitwas continued for 24 h
  5. customthe crude mixture was purified by column chromatography (Si—PCC, gradient 0-40% EtOAc in cyclohexane)

출처 및 근거

ORD 기록
ord-2a4d9e47d52845039fa83e2905db9bcd
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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