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Methanesulfonyl chloride → tert-butyl (6R,7R)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-3-(oxolan-3-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1421805
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HRID 1421805 반응식
Cl.[CH3:2][O:3]/[N:4]=[C:5](/[C:9]1[N:10]=[C:11]([NH:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:12][CH:13]=1)\[C:6]([OH:8])=O.CS(Cl)(=O)=O.C(N(C(C)C)CC)(C)C.[NH2:48][C@@H:49]1[C:68](=[O:69])[N:51]2[C:52]([C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])=[C:53]([CH:56]3[CH2:60][CH2:59][O:58][CH2:57]3)[CH2:54][S:55][C@H:50]12>CN(C=O)C.N1C=CC=CC=1>[CH3:2][O:3]/[N:4]=[C:5](/[C:9]1[N:10]=[C:11]([NH:14][C:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[S:12][CH:13]=1)\[C:6]([NH:48][C@@H:49]1[C:68](=[O:69])[N:51]2[C:52]([C:61]([O:63][C:64]([CH3:65])([CH3:66])[CH3:67])=[O:62])=[C:53]([CH:56]3[CH2:60][CH2:59][O:58][CH2:57]3)[CH2:54][S:55][C@H:50]12)=[O:8]
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참가 물질

7

반응물 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 95660662-(Tritylamino)-alpha-(methoxyimino)-4-thiazoleacetic acid, predominantly syn hydrochlorideHCID 54127982t-Butyl (6R,7R)-7-Amino-3-[(RS)-tetrahydrofuran-3-yl]ceph-3-em-4-carboxylate

생성물 1

HCID 141582263
tert-butyl (6R,7R)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-3-(oxolan-3-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6228Dimethylformamide용매2회

실험 절차

2-(Z)-Methoxyimino-2-(2-tritylaminothiazol-4-yl)acetic acid hydrochloride (0.751 g) in DMF (5 ml) was treated with methanesulphonyl chloride (0.179 g, 0.121 ml) and diisopropylethylamine (0.404 g, 0.544 ml) as described in Example 1(g). This was then treated with t-butyl (6R,7R)-7-amino-3-[(RS)-tetrahydrofuran-3-yl]ceph-3-em-4-carboxylate (0.464 g) and pyridine (0.112 g, 0.114 ml) in DMF (5 ml). Following work up and purification by flash chromatography with 40, 50 and 60% ethyl acetate/hexane, the title compound was obtained as a yellow foam (0.874 g, 82%); νmax (CH2Cl2) 3398, 1783, 1731 (shoulder), 1718 and 1688 cm-1 ; δH (CDCl3) 1.53 (9H, s), 1.69-2.43 (3H, m's), 3.29 and 3.46 with 3.34 and 3.48 (2H, 2ABq's, J 17.7 and 17.7 Hz), 3.63-4.07 (6H, m's and s), 5.03 and 5.06 (1H, 2d's, J 4.8 and 4.8 Hz), 5.84-5.90 (1H, m), 6.73 and 6.74 (1H, 2s), 6.76 and 6.90 (1H, 2d's, J 8.7 and 8.7 Hz exchangeable with D2O), 7.02 (1H, br. s, exchangeable with D2O) and 7.31 (15H, s). [Mass spectrum: +ve ion (3NOBA, Na+) MNa+ (774)].

후처리

  1. custompurification by flash chromatography with 40, 50 and 60% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-50f5a11eb9c94f0495839897f7a0474d
출처 데이터셋
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06077952

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