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

HRID 376565노트

반응식

HRID 376565 반응식
CS(Cl)(=O)=O.[C:6]([NH:25][C:26]1[S:27][CH:28]=[C:29](/[C:31](=[N:35]/[O:36][C:37]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)/[C:32]([O-])=[O:33])[N:30]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Na+].[NH2:57][C@@H:58]1[C:77](=[O:78])[N:60]2[C:61]([C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])=[C:62]([C@H:65]3[CH2:69][CH2:68][CH2:67][O:66]3)[CH2:63][S:64][C@H:59]12.N1C=CC=CC=1>CN(C=O)C.C(OCC)(=O)C>[O:66]1[CH2:67][CH2:68][CH2:69][C@@H:65]1[C:62]1[CH2:63][S:64][C@@H:59]2[C@H:58]([NH:57][C:32](=[O:33])/[C:31](/[C:29]3[N:30]=[C:26]([NH:25][C:6]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[S:27][CH:28]=3)=[N:35]\[O:36][C:37]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:77](=[O:78])[N:60]2[C:61]=1[C:70]([O:72][C:73]([CH3:75])([CH3:74])[CH3:76])=[O:71]

참가 물질

7

반응물 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 10381740t-butyl (6R,7R)-7-amino-3-[(R)-tetrahydrofuran-2-yl]ceph-3-em-4-carboxylateHCID 23714200sodium (2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetate

생성물 1

HCID 172930684tert-butyl (6R,7R)-8-oxo-3-[(2R)-oxolan-2-yl]-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate수율 68%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

Methanesulphonyl chloride (96μl, 1.25mmol) was added to sodium 2-(2-tritylaminothiazol-4-yl)-2-(Z)-trityloxyiminoacetate (852mg, 1.2mmol) in DMF (2ml) at <-40° C. The mixture was stirred 0.5h at -30±10° C. then t-butyl (6R,7R)-7-amino-3-[(R)-tetrahydrofuran-2-yl]ceph-3-em-4-carboxylate (326mg, 1mmol) in DMF (2ml), followed by pyridine (101μl, 1.25mmol), were added. The reaction was stirred for 1h without further cooling then diluted with ethyl acetate, washed twice with water and with brine, dried, concentrated in vacuo and flash chromatographed eluting with 25, 30% ethyl acetate in hexane to give the title compound as a colourless foam (665mg, 68%); vmax (CH2Cl2) 3395, 1787, 1722, 1687, 1527, 1449, 1156 and 1051cm-1 ; δH (CDCl3 /CD3OH) 1.55 (9H, s), 1.65-2.25 (4H, m), 3.32 and 3.40 (2H, ABq, J 17.6Hz), 3.8-4.0 (2H, m), 5.08 (1H, d, J 4.8Hz), 5.13 (1H, dd, J 7.0, 8.1Hz), 5.91 (1H, d, J 4.5Hz), 6.56 (1H, s), 7.2-7.5 (30H, m). [Mass spectrum: +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (1002)].

후처리

  1. additionwere added
  2. temperaturewithout further cooling
  3. washwashed twice with water and with brine
  4. customdried
  5. concentrationconcentrated in vacuo and flash
  6. customchromatographed
  7. washeluting with 25, 30% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-9bae6efc9c4e42f0a95829a95fdf6f4c
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06020329

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