Trisodium citrate → HCID 172918144, compound

HRID 376608Notes

Reaction equation

HRID 376608 reaction equation
C1(OC)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:13][O:14][C:15]([C@@H:17]1[O:21][C@H:20]([C:22]2[CH2:23][S:24][C@@H:25]3[C@H:41]([NH:42][C:43](=[O:54])/[C:44](/[C:48]4[N:49]=[C:50]([NH2:53])[S:51][CH:52]=4)=[N:45]\[O:46][CH3:47])[C:40](=[O:55])[N:26]3[C:27]=2[C:28]([O:30]CC2C=CC(OC)=CC=2)=[O:29])[CH2:19][CH2:18]1)=[O:16].C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O.[Na+:69].[Na+].[Na+]>ClCCl>[NH2:53][C:50]1[S:51][CH:52]=[C:48](/[C:44](=[N:45]/[O:46][CH3:47])/[C:43]([NH:42][C@@H:41]2[C:40](=[O:55])[N:26]3[C:27]([C:28]([O-:30])=[O:29])=[C:22]([C@@H:20]4[CH2:19][CH2:18][C@H:17]([C:15]([O:14][CH3:13])=[O:16])[O:21]4)[CH2:23][S:24][C@H:25]23)=[O:54])[N:49]=1.[Na+:69]

Participants

6

Reactant 4

HCID 6224Trisodium citrateHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 172938119HCID 172938119, compound

Product 1

HCID 172918144HCID 172918144, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

A stirred solution of anisole (0.75ml) and dichloromethane (0.38ml) was cooled to -20° C. and aluminium chloride (19mg) was added. The mixture was stirred at the same temperature for 15min. and then cooled to -40° C., and then a solution of 4-methoxybenzyl (6R,7R)-3-[(2S,5R)-5-methoxycarbonyltetrahydrofuran-2-yl]-7-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]ceph-3-em-4-carboxylate (31mg) in dichloromethane (2.5ml) was added and the mixture stirred at the same temperature for 5min. Trisodium citrate (1.64ml of 0.5M solution) was then added and the mixture stirred for 10 min at room temperature. The aqueous phase was separated and washed twice with dichloromethane. The solution was evaporated and the product isolated by column chromatography of the residue (HP20SS, water with increasing proportions of acetone as eluent). Fractions containing product were combined, evaporated and the residue dissolved in water (3ml) and freeze dried to give the title compound (12mg); vmax (KBr) 1762, 1670 and 1604cm-1 ; δH [(CD3)2SO)]1.50-1.63 (1H, m), 1.90-2.26 (3H, m), 3.30-3.47 (2H, m), 3.65 (3H, s), 3.83 (3H, s), 4.39 (1H, dd, J 3.4, 8.7Hz), 4.98 (1H, d, J 4.8Hz), 5.0 (1H, dd, J 5.1, 9.8Hz), 5.52 (1H, dd, J 4.7, 8.2Hz), 6.75 (1H, s), 7.24 (2H, s) and 9.49 (1H, d, J 8.1Hz).

Workup

  1. stirringthe mixture stirred at the same temperature for 5min
  2. stirringthe mixture stirred for 10 min at room temperature
  3. customThe aqueous phase was separated
  4. washwashed twice with dichloromethane
  5. customThe solution was evaporated
  6. customthe product isolated by column chromatography of the residue (HP20SS, water with increasing proportions of acetone as eluent)
  7. additionFractions containing product
  8. customevaporated
  9. dissolutionthe residue dissolved in water (3ml)
  10. customfreeze dried

Sources & evidence

ORD record
ord-543cb740373349959cc6c479a432077c
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

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