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Diisopropylethylamine → 4-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-tetrahydro-pyran-3-carboxylic acid methyl ester

HRID 736736
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HRID 736736 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH:10]([NH2:11])[CH2:9][CH2:8][O:7][CH2:6]1)=[O:4].Cl.[CH3:13][C:14]1[CH:23]=[C:22]([CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:1][O:2][C:3]([CH:5]1[CH:10]([NH:11][S:32]([C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:24][C:22]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=[C:14]([CH3:13])[CH:23]=3)=[CH:27][CH:28]=2)(=[O:33])=[O:34])[CH2:9][CH2:8][O:7][CH2:6]1)=[O:4]
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 20747811methyl 4-aminotetrahydro-2H-pyran-3-carboxylateHCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride

생성물 1

HCID 688172194-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-tetrahydro-pyran-3-carboxylic acid methyl ester수율 82.3%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
25 °C

실험 절차

To a mixture of 0.5 g (2.79 mmol) of 4-amino-tetrahydro-pyran-3-carboxylic acid methyl ester [WO 01/70673, Example 207] and 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride (1.0 g, 2.94 mmol) in N,N-dimethylformamide (10 mL) was added N,N-diisopropylethylamine (1.02 mL, 5.88 mmol) at 0° C. The solution was allowed to warm to 25° C. over 19 h. The DMF was removed in vacuo and the resulting solid was partitioned between ethyl acetate (100 mL) and water (30 mL). The aqueous layer was washed with ethyl acetate (2×50 mL). ). The organic layer was dried over MgSO4, filtered and concentrated to obtain a crude oil (1.48 g). The crude product was purified by Biotage Flash 40M chromatography, eluting with 1:4 ethyl acetate-hexanes, to afford 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-tetrahydro-pyran-3-carboxylic acid methyl ester as a white solid (1.08 g, 78%). MS: 471 (M+H)+

후처리

  1. customThe DMF was removed in vacuo
  2. customthe resulting solid was partitioned between ethyl acetate (100 mL) and water (30 mL)
  3. washThe aqueous layer was washed with ethyl acetate (2×50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain a crude oil (1.48 g)
  8. customThe crude product was purified by Biotage Flash 40M chromatography
  9. washeluting with 1:4 ethyl acetate-hexanes

출처 및 근거

ORD 기록
ord-095880805f6e4f16a26a4d208a4cda9d
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07595327B2

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