Trisodium citrate → HCID 131721627, compound

HRID 376589Notes

Reaction equation

HRID 376589 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[CH:37]/[CH2:38][CH3:39])/[C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:23]([O:25]CC4C=CC(OC)=CC=4)=[O:24])=[C:15]([C@@H:18]4[CH2:22][CH2:21][CH2:20][O:19]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Cl-].[Al+3].[Cl-].[Cl-].C1(OC)C=CC=CC=1.C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O.[Na+:65].[Na+].[Na+]>ClCCl.O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[CH:37]/[CH2:38][CH3:39])/[C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:23]([O-:25])=[O:24])=[C:15]([C@@H:18]4[CH2:22][CH2:21][CH2:20][O:19]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+:65]

Participants

7

Reactant 4

HCID 6224Trisodium citrateHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 131721628HCID 131721628, compound

Product 1

HCID 131721627HCID 131721627, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-40 °C

Procedure

4-Methoxybenzyl (6R,7R)-7-[2-(2-aminothiazol-4-yl)-(Z)-pent-2-enamido]-3-[(S)-tetrahydrofuran-2-yl]ceph-3-em-4-carboxylate (80mg) in dichloromethane (2ml) was added dropwise to a mixture of aluminium chloride (47mg) and anisole (1.03ml) in dichloromethane (2ml) at -50° C. under argon. The mixture was stirred for 15 minutes at -40° C. and 0.5M trisodium citrate (3.42ml) added, stirred at room temperature for 15 minutes then diluted with dichloromethane (10ml) and water (10ml). The aqueous layer was collected, washed with dichloromethane and chromatographed on HP20SS eluting with 0, 1, 2, 5 and 10% acetone in water. Fractions containing the product, h.p.l.c analysis, were combined, concentrated and freeze-dried to give the title compound (22mg); vmax (KBr) 3407, 1757, 1609, 1527, 1375, 1338 and 1041 cm-1 ; δH (D2O, 250MHz) 1.03 (3H,t,J 7.5Hz), 1.65-2.30 (6H,m), 3.32 and 3.51 (2H, ABq, J 7.7Hz), 3.70-3.95 (2H,m), 4.65-4.80 (1H,m), 5.20 (1H,d,J 4.7Hz), 5.74 (1H,d,J 4.7Hz), 6.33 (1H,t,J 8Hz) and 6.47 (1H,s). [Mass spectrum +ve ion (thioglycerol) MH+ (473)].

Workup

  1. stirringstirred at room temperature for 15 minutes
  2. customThe aqueous layer was collected
  3. washwashed with dichloromethane
  4. customchromatographed on HP20SS
  5. washeluting with 0, 1, 2, 5 and 10% acetone in water
  6. additionFractions containing the product, h.p.l.c analysis
  7. concentrationconcentrated
  8. customfreeze-dried

Sources & evidence

ORD record
ord-e1718c8f3224478ea61765afd735af36
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

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