4-Methylmorpholine → N'-phenyloxamide

HRID 1968429노트

반응식

HRID 1968429 반응식
[C:1]1([NH:7][C:8](=[O:12])[C:9](O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C[N:16]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CN1CCOCC1.C(N)(=O)C(N)=O>C(Cl)Cl.C(OCC)(=O)C>[C:1]1([NH:7][C:8](=[O:12])[C:9]([NH2:16])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 79724-Methylmorpholine2회HCID 10113OxamideHCID 10378Oxanilic acidHCID 2724699PyBOP

생성물 1

HCID 596227N'-phenyloxamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

Acid 84 (20 mg, 1.4 eq) in CH2Cl2 (1 mL) was treated with PyBOP (53 mg, 1.2 eq) and NMM (0.028 mL, 3.0 eq) and stirred for 5 minutes. To this was added a solution of oxalamide (50 mg, 1.0 eq) and NMM (0.028 mL, 3.0 eq) in CH2Cl2 (1 mL) and the mixture stirred at room temperature overnight. The mixture was diluted with ethyl acetate, the organic phase washed with 0.5N HCl, brine, saturated bicarbonate solution, and brine, then dried over sodium sulfate, filtered and concentrated in vacuo. Purification by preparative HPLC yielded 24 mg (38%) of N-[cyclohexyl-(1-{2-[1-cyclopropylcarbamoyl-hydroxy-methyl)-butylcarbamoyl]-octahydro-indole-1-carbonyl}-2,2-dimethyl-propylcarbamoyl)methyl]-N′-phenyl-oxalamide 96 as a white solid with consistent analytical data. LCMS ret time=4.07, M+H=737.26, M−H=735.22.

후처리

  1. stirringthe mixture stirred at room temperature overnight
  2. washthe organic phase washed with 0.5N HCl, brine, saturated bicarbonate solution, and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative HPLC

출처 및 근거

ORD 기록
ord-8c08600d570d473495a8be6c8464ad6e
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426359B2

반응 노트

불러오는 중…