Potassium Carbonate → 1-propan-2-yloxycarbonyloxyethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[(2S)-oxolan-2-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 376595ノート

反応式

HRID 376595 の反応式
I[CH:2]([O:4][C:5]([O:7][CH:8]([CH3:10])[CH3:9])=[O:6])[CH3:3].[NH2:11][C:12]1[S:13][CH:14]=[C:15](/[C:17](=[N:38]/[O:39][CH3:40])/[C:18]([NH:20][C@@H:21]2[C:36](=[O:37])[N:23]3[C:24]([C:33]([O-:35])=[O:34])=[C:25]([C@@H:28]4[CH2:32][CH2:31][CH2:30][O:29]4)[CH2:26][S:27][C@H:22]23)=[O:19])[N:16]=1.[Na+].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.C(OCC)(=O)C>[NH2:11][C:12]1[S:13][CH:14]=[C:15](/[C:17](=[N:38]/[O:39][CH3:40])/[C:18]([NH:20][C@@H:21]2[C:36](=[O:37])[N:23]3[C:24]([C:33]([O:35][CH:2]([O:4][C:5]([O:7][CH:8]([CH3:10])[CH3:9])=[O:6])[CH3:3])=[O:34])=[C:25]([C@@H:28]4[CH2:32][CH2:31][CH2:30][O:29]4)[CH2:26][S:27][C@H:22]23)=[O:19])[N:16]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 110106451-Iodoethyl isopropyl carbonateHCID 23690298Cefovecin sodium

生成物 1

HCID 1415822621-propan-2-yloxycarbonyloxyethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[(2S)-oxolan-2-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate収率 19.9%

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-iodo-1-(propan-2-yl)oxycarbonyloxyethane (516mg) in 1-methyl-2-pyrrolidinone (2ml) was added dropwise over 45 mins 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 (237mg) and finely powdered potassium carbonate (276mg) in 1-methyl-2-pyrrolidinone (5ml). The mixture was stirred for an additional 15 mins, diluted with ethyl acetate, washed with water, brine, dried (magnesium sulphate), concentrated and flash chromatographed on silica gel eluting with 50, 60, 70, 80% ethyl acetate in hexane to give the title compound as a foam (58mg); vmax (CHCl3) 2960, 1787, 1760, 1682, 1633, 1519 and 1377cm-1 ; δ(CDCl3, 250MHz) 1.20-2.50 (13H, m), 3.35-3.80 (2H, m), 3.80-4.20 (2H, m), 4.22 (3H, s), 4.83-5.10 (2H, m), 5.85-6.00 (1H, m), 6.85-7.08 (1H, m), 7.27 (1H, s) and 7.76 (1H, br, m). [Mass spectrum: +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (606)].

後処理

  1. washwashed with water, brine
  2. dry with materialdried (magnesium sulphate)
  3. concentrationconcentrated
  4. customflash chromatographed on silica gel eluting with 50, 60, 70, 80% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-be0e1741156d4b7685ce58cabd7ead6a
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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