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 376565ノート

反応式

HRID 376565 の反応式
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]

参加物

7

反応物 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

生成物 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-carboxylate収率 68%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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)].

後処理

  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

出典と根拠

ORDレコード
ord-9bae6efc9c4e42f0a95829a95fdf6f4c
出典データセット
uspto-grants-2000_02
特許番号
US06020329

反応ノート

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