Trisodium citrate → HCID 88208257, compound

HRID 581208Notes

Reaction equation

HRID 581208 reaction equation
C1(OC)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[NH2:13][C:14]1[S:15][CH:16]=[C:17](/[C:19](=[N:49]/[O:50][CH3:51])/[C:20]([NH:22][C@@H:23]2[C:30](=[O:31])[N:29]3[C@@H:24]2[CH2:25][O:26][C:27]([CH:44]2[CH2:48][CH2:47][CH2:46][O:45]2)=[C:28]3[C:32]([O:34]CC2C=CC(OC)=CC=2)=[O:33])=[O:21])[N:18]=1.C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O.[Na+:65].[Na+].[Na+]>ClCCl>[NH2:13][C:14]1[S:15][CH:16]=[C:17](/[C:19](=[N:49]/[O:50][CH3:51])/[C:20]([NH:22][C@@H:23]2[C:30](=[O:31])[N:29]3[C@@H:24]2[CH2:25][O:26][C:27]([CH:44]2[CH2:48][CH2:47][CH2:46][O:45]2)=[C:28]3[C:32]([O-:34])=[O:33])=[O:21])[N:18]=1.[Na+:65]

Participants

6

Reactant 4

HCID 6224Trisodium citrateHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 140399827(4-methoxyphenyl)methyl (6S,7S)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(oxolan-2-yl)-4-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 88208257HCID 88208257, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

A stirred mixture of anisole (2.38 ml) and dichloromethane (1.2 ml) under argon was cooled to -20° C. and treated with aluminium chloride (61 mg). The mixture was stirred at -20° C. for 15 min. and then a slurry of 4-methoxybenzyl (6S,7S)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-8-oxo-3-(tetrahydrofuran-2-yl)-1-aza-4-oxabicyclo[4.2.0]oct-2-ene-2-carboxylate (I) (88 mg) in dichloromethane (7.5 ml) was added. The mixture was stirred for 5 min. and then trisodium citrate (5.2 ml of 0.5M) was added and the mixture stirred for 10 min. The aqueous phase was separated and washed twice with dichloromethane, then evaporated. The product was purified by HP20SS chromatography of the residue (water with increasing proportions of acetone as eluent). Fractions containing product were combined and evaporated and the residue dissolved in water (4 ml) and freeze-dried to give the title compound (27 mg). νmax (KBr) 1757, 1662 and 1617 cm-1 ; δ[(CD3)2SO] 1.68-1.95 (4H, m), 3.58-3.77 (4H, m), 3.84 (3H, s), 4.35 (1H, m), 5.51 (1H, dd, J 3.91 and 8.83 Hz), 5.68 (1H, t, J 6.84), 6.78 (1H, s), 7.25 (2H, s), 9.91 (1H, d, J 8.83 Hz).

Workup

  1. stirringThe mixture was stirred for 5 min.
  2. stirringthe mixture stirred for 10 min
  3. customThe aqueous phase was separated
  4. washwashed twice with dichloromethane
  5. customevaporated
  6. customThe product was purified by HP20SS chromatography of the residue (water with increasing proportions of acetone as eluent)
  7. additionFractions containing product
  8. customevaporated
  9. dissolutionthe residue dissolved in water (4 ml)
  10. customfreeze-dried

Sources & evidence

ORD record
ord-28220c5688f44e329f4485f5c5506935
Source dataset
uspto-grants-1999_07
Patent number
US05919925

Reaction notes

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