2-(2-Bromoethoxy)tetrahydro-2H-pyran → Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-(2-hydroxyethyl)carbamate

HRID 1597803노트

반응식

HRID 1597803 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH2:23][CH2:24][O:25]C2CCCCO2)[C:19](=[O:22])[O:20][CH3:21])=[C:14]([CH3:32])[CH:13]=1.S1C2C=CC=CC=2N=C1COC1C=CC(NC(=O)OC)=C(C)C=1.O1CCCCC1OCCBr.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH2:23][CH2:24][OH:25])[C:19](=[O:22])[O:20][CH3:21])=[C:14]([CH3:32])[CH:13]=1

참가 물질

7

반응물 4

HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 18932257methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]carbamateHCID 18932260Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-[2-(2-tetrahydropyranyloxy)ethyl]carbamate2회

생성물 1

HCID 18932407Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-(2-hydroxyethyl)carbamate수율 94.1%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-[2-(2-tetrahydropyranyloxy)ethyl]carbamate (Compound No. D1.119) was first prepared from methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]carbamate (Compound No. C1.5, prepared as described in Example 21 below) and 2-(2-tetrahydropyranyloxy)ethyl bromide according to the general procedure of Example 13 above. A catalytic amount (approximately 10 mg) of p-toluenesulfonic acid monohydrate was added to a solution of 658.1 mg of the thus prepared methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-[2-(2-tetrahydropyranyloxy)ethyl]carbamate in 6.6 ml of methanol at room temperature. The resulting mixture was stirred for 2 hours at room temperature, and water was then added to the reaction mixture. The resulting mixture was extracted with ethyl acetate and the organic layer was washed consecutively with water and a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure to give a residue which was purified by column chromatography through silica gel using a 1:2 by volume mixture of hexane and ethyl acetate as the eluent, to give 702.5 mg (yield 94.1%) of the title compound as a solid having a melting point of 109°-110° C.

후처리

  1. customC1.5, prepared
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe organic layer was washed consecutively with water
  4. dry with materiala saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate
  5. customThe solvent was then removed by evaporation under reduced pressure
  6. customto give a residue which
  7. customwas purified by column chromatography through silica gel using a 1:2
  8. additionby volume mixture of hexane and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-74f38528465946ad9b6e4d6c1c46ca6d
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05736487

반응 노트

불러오는 중…