Acetone → 3-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-5-yl methylcarbamate

HRID 1292521노트

반응식

HRID 1292521 반응식
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[C:14]3[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:13]=3[O:12][N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:20][N:21]=[C:22]=[O:23].CC(C)=O.C(Cl)Cl>CCOC(C)=O.[Cu]Cl>[CH3:20][NH:21][C:22](=[O:23])[O:19][C:16]1[CH:17]=[CH:18][C:13]2[O:12][N:11]=[C:10]([NH:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[C:14]=2[CH:15]=1

참가 물질

7

반응물 4

HCID 180AcetoneHCID 6344DichloromethaneHCID 12228Methyl IsocyanateHCID 187964613-[[2-(4-Morpholinyl)ethyl]-amino]-1,2-benzisoxazol-5-ol

생성물 1

HCID 187964473-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-5-yl methylcarbamate수율 32.9%

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]-amino]-1,2-benzisoxazol-5-ol (1 g) and a catalytic amount of copper(I)chloride (0.05 g) in EtOAc (100 ml) was added methyl isocyanate (0.26 g). After 24 hours TLC (silica gel, 1:1:20 acetone/MeOL/DCM) showed no starting material. The reaction was filtered through neutral alumina eluting with EtOAc (1 l) and the filtrate was concentrated in vacuo. The residue was further purified by flash chromatography (silica gel) eluting with 1:1:20 acetone/MeOH/DCM to yield 0.4 g of the product, m.p. 135°-136° C.

후처리

  1. filtrationThe reaction was filtered through neutral alumina eluting with EtOAc (1 l)
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was further purified by flash chromatography (silica gel)
  4. washeluting with 1:1:20 acetone/MeOH/DCM

출처 및 근거

ORD 기록
ord-3e4b42ccb3a94495ae4c8856feace7f3
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05756754

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