Potassium Carbonate → HCID 88258899、化合物

HRID 1421813ノート

反応式

HRID 1421813 の反応式
[C:1]([O:4][CH:5](Br)[CH3:6])(=[O:3])[CH3:2].[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:35]/[O:36][CH3:37])/[C:15]([NH:17][C@@H:18]2[C:33](=[O:34])[N:20]3[C:21]([C:30]([O-:32])=[O:31])=[C:22]([C@@H:25]4[CH2:29][CH2:28][CH2:27][O:26]4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1.[Na+].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.C(OCC)(=O)C>[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:35]/[O:36][CH3:37])/[C:15]([NH:17][C@@H:18]2[C:33](=[O:34])[N:20]3[C:21]([C:30]([O:32][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH3:6])=[O:31])=[C:22]([C@@H:25]4[CH2:29][CH2:28][CH2:27][O:26]4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 111375051-Bromoethyl acetateHCID 23690298Cefovecin sodium

生成物 1

HCID 88258899HCID 88258899、化合物収率 79.8%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒2 回

実験手順

A solution of (RS)-1-acetoxyethylbromide (267 mg) in 1-methyl-2-pyrrolidinone (2 ml) was added dropwise, over 1 hour, to an ice cold mixture of sodium (6R,7R)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-[(S)-tetrahydrofuran-2-yl]ceph-3-em-4-carboxylate (190 mg) and potassium carbonate (110 mg) in 1-methyl-2-pyrrolidinone (1 ml). After 15 minutes the mixture was diluted with ethyl acetate, washed with water, brine, dried (MgSO4), concentrated and flash chromatographed on silica gel eluting with 50,70,80 and 90% ethyl acetate in hexane to give the title compound (172 mg); νmax (CHCl3) 3019, 2929, 1786, 1683, 1520, 13176 and 1135 cm-1 ; δH (CDCl3, 250 MHz) 1.45-1.75 (4H,m), 1.90-2.10 (2H,m), 2.09 and 2.10 (together 3H, 2s), 2.30-2.50 (1H,m), 3.36 and 3.65 (2H, ABq, J 18.8 Hz), 4.93-5.10 (2H,m), 5.90-6.05 (1H,m), 6.94 and 7.07 (together 1H,q,J 5.8 Hz), 7.10 and 7.15 (together 1H, 2s) and 7.60 and 7.67 (together 1H,2d, J 7.4 Hz); [Mass spectrum: +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (562)].

後処理

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customflash chromatographed on silica gel eluting with 50,70,80 and 90% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-951c75de1b0f44be94d8d794f03f949d
出典データセット
uspto-grants-2000_06
特許番号
US06077952

反応ノート

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