Triethylamine → HCID 141573153, compound

HRID 1587722Notes

Reaction equation

HRID 1587722 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:39]/[O:40][C:41]([C:44]([OH:46])=[O:45])([CH3:43])[CH3:42])/[C:8]([NH:10][CH:11]2[C:37](=[O:38])[N:13]3[C:14]([C:34]([OH:36])=[O:35])=[C:15]([CH2:18][NH:19][CH2:20][C:21]4[CH:26]=[C:25]([OH:27])[C:24]([OH:28])=[CH:23][C:22]=4[CH2:29][C:30](OC)=[O:31])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(N(CC)CC)C>C(#N)C.O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:39]/[O:40][C:41]([C:44]([OH:46])=[O:45])([CH3:43])[CH3:42])/[C:8]([NH:10][CH:11]2[C:37](=[O:38])[N:13]3[C:14]([C:34]([OH:36])=[O:35])=[C:15]([CH2:18][N:19]4[C:30](=[O:31])[CH2:29][CH:22]5[C:21](=[CH:26][C:25]([OH:27])=[C:24]([OH:28])[CH2:23]5)[CH2:20]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 88403737HCID 88403737, compound

Product 1

HCID 141573153HCID 141573153, compoundYield 7.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 7-[2-(2-aminothiazol-4-yl)-2-((Z)-1-carboxy-1-methylethoxyimino)acetamido]-3-(4,5-dihydroxy-2-methoxycarbonylmethylbenzylaminomethyl)ceph-3-em-4-carboxylic acid (800 mg) in acetonitrile (5 ml) and water (5 ml), at 0° C., was added triethylamine (260 μl). The mixture was stirred, at ambient temperature, for 90 minutes and evaporated under reduced pressure. The residue was dissolved in water (25 ml) containing acetic acid (a few drops) and sodium acetate, filtered and purified by chromatography (HPLC; Dynamax column) using 17.5% acetonitrile/water. Freeze-drying afforded the title compound (58 mg); NMR (DMSO-d6 /CF3COOH) 1.49(s,3H); 1.52(s,3H); 3.35(dd,2H); 3.4(s,3H); 4.3(m,2H); 4.5(dd,2H); 5.18(d,1H); 5.85(dd,1H); 6.58(d,1H); 6.62(s,1H); 9.7(d,1H): FAB M/S (M-H)- 645.

Workup

  1. customevaporated under reduced pressure
  2. dissolutionThe residue was dissolved in water (25 ml)
  3. additioncontaining acetic acid (a few drops) and sodium acetate
  4. filtrationfiltered
  5. custompurified by chromatography (HPLC; Dynamax column)
  6. customFreeze-drying

Sources & evidence

ORD record
ord-8174c969e0754d538ad81072e2a0cc8f
Source dataset
uspto-grants-1993_06
Patent number
US05219848

Reaction notes

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