4-Methylmorpholine → N'-phenyloxamide

HRID 1968429ノート

反応式

HRID 1968429 の反応式
[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

参加物

7

反応物 4

HCID 79724-Methylmorpholine2 回HCID 10113OxamideHCID 10378Oxanilic acidHCID 2724699PyBOP

生成物 1

HCID 596227N'-phenyloxamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8c08600d570d473495a8be6c8464ad6e
出典データセット
uspto-grants-2013_04
特許番号
US08426359B2

反応ノート

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