Benzenesulfinic acid, sodium salt → Methyl 4-[5-methyl-4-[(phenylsulfonyl)methyl]-1,3-oxazol-2-yl]benzoate

HRID 931423

반응식

HRID 931423 반응식
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[C:19]1([S:25]([O-:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Na+]>>[CH3:8][C:7]1[O:6][C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[N:4][C:3]=1[CH2:2][S:25]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:27])=[O:26]

참가 물질

3

반응물 2

HCID 2723840Benzenesulfinic acid, sodium saltHCID 23076573Methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate

생성물 1

HCID 68278169Methyl 4-[5-methyl-4-[(phenylsulfonyl)methyl]-1,3-oxazol-2-yl]benzoate수율 84%

실험 절차

Reaction of chloride 2 (267 mg, 1.0 mmol) and sodium benzenesulfinate (173 mg, 1.1 mmol) gave benzoate 16 (311 mg, 84%) as a white powder: mp (EtOAc) 159-161° C.; 1H NMR (CDCl3) δ 8.07 (ddd, J=8.7, 1.9, 1.5 Hz, 2H, H-2, H-6), 7.91 (ddd, J=8.7, 1.9, 1.5 Hz, 2H, H-3, H-5), 7.82 (ddd, J=8.2, 2.0, 1.2 Hz, 2H, H-2′, H-6′), 7.64 (tt, J=7.5, 1.2 Hz, 1H, H-4′), 7.52 (br dd, J=8.2, 7.5 Hz, 2H, H-3′, H-5′), 4.32 (s, 2H, CH2SO2), 3.94 (s, 3H, OCH3), 2.32 (s, 3H, CH3); MS m/z 372.3 (MH+, 100%). Anal. calcd for C19H17NO5S: C, 61.44; H, 4.61; N, 3.77. Found: C, 61.75; H, 4.62; N, 3.75%.

출처 및 근거

ORD 기록
ord-10d2751a011f4ac7a30bcf35c47cbd8c
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296732B2

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