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Diisopropylethylamine → 3,5-Dichlorobenzyl 2-(2-(N-methyl-2-oxo-2,3-dihydrooxazole-5-carboxamido)ethyl)morpholine-4-carboxylate

HRID 1480386
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HRID 1480386 반응식
[CH3:1][NH:2][CH2:3][CH2:4][CH:5]1[O:10][CH2:9][CH2:8][N:7]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=2)=[O:12])[CH2:6]1.[O:23]=[C:24]1[NH:28][CH:27]=[C:26]([C:29](O)=[O:30])[O:25]1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:1][N:2]([CH2:3][CH2:4][CH:5]1[O:10][CH2:9][CH2:8][N:7]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[C:17]([Cl:22])[CH:18]=[C:19]([Cl:21])[CH:20]=2)=[O:12])[CH2:6]1)[C:29]([C:26]1[O:25][C:24](=[O:23])[NH:28][CH:27]=1)=[O:30]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 539814232-Hydroxy-1,3-oxazole-5-carboxylic acidHCID 867226373,5-Dichlorobenzyl 2-(2-(methylamino)ethyl)morpholine-4-carboxylate

생성물 1

HCID 762863523,5-Dichlorobenzyl 2-(2-(N-methyl-2-oxo-2,3-dihydrooxazole-5-carboxamido)ethyl)morpholine-4-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

A mixture comprising of 3,5-dichlorobenzyl 2-(2-(methylamino)ethyl)morpholine-4-carboxylate (step 2)(169 mg, 0.487 mmol), 2-oxo-2,3-dihydrooxazole-5-carboxylic acid ((Example 21, step 1)) (161 mg, 0.487 mmol), T3P® (50% in DMF) (426 μl, 0.730 mmol) and Huenig's base (425 μl, 2.433 mmol) in DMF (1622 μl) was stirred at room temperature for 20 hours. The resulting mixture was diluted with EtOAc and washed with water. The organic portion was dried with MgSO4, filtered and concentrated under reduced pressure. The crude material was dry loaded with silica onto an ISCO 4 g column eluting with 0-100% EtOAc (1% acetic acid) in iso-hexane. The product fractions were concentrated under reduced pressure to afford the title compound;

후처리

  1. washwashed with water
  2. dry with materialThe organic portion was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dry with materialThe crude material was dry
  6. washeluting with 0-100% EtOAc (1% acetic acid) in iso-hexane
  7. concentrationThe product fractions were concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e0dc003004fe4d28ab49b198ea48458d
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409895B2

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