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 376595노트

반응식

HRID 376595 반응식
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

참가 물질

6

반응물 3

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

생성물 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-carboxylate수율 19.9%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매2회

실험 절차

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)].

후처리

  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

출처 및 근거

ORD 기록
ord-be0e1741156d4b7685ce58cabd7ead6a
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06020329

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