Methanol → HCID 21314184, compound

HRID 1579964Notes

Reaction equation

HRID 1579964 reaction equation
[Cl:1][C:2]1([CH3:34])[CH2:9][S:8][CH:7]2[N:4]([C:5](=[O:20])[CH:6]2[NH:10]C(=O)CC2C=CC=CC=2)[CH:3]1[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:22].P(Cl)(Cl)(Cl)(Cl)Cl.CN(C)C1C=CC=CC=1.CO>ClCCl>[N+:31]([C:28]1[CH:27]=[CH:26][C:25]([CH2:24][O:23][C:21]([CH:3]2[C:2]([Cl:1])([CH3:34])[CH2:9][S:8][CH:7]3[N:4]2[C:5](=[O:20])[CH:6]3[NH2:10])=[O:22])=[CH:30][CH:29]=1)([O-:33])=[O:32]

Participants

6

Reactant 4

HCID 887MethanolHCID 949N,N-DimethylanilineHCID 24819Phosphorus pentachlorideHCID 21500060HCID 21500060, compound

Product 1

HCID 21314184HCID 21314184, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To an ice cold solution of 3-chloro-3-methyl-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acid, p-nitrobenzyl ester (5.04 g, 10 mmoles) in 100 ml of dichloromethane, are added in rapid succession phosphorus pentachloride (3.1 g, 15 mmoles) and N,N-dimethylaniline (1.8 g, 15 mmoles). The mixture is stirred at 0°C. for 15 minutes and at 25°C. for 3 hours, then 30 ml. of absolute methyl alcohol is added and the solution is further stirred for 1 hour. The solvent is flash evaporated. To the residue are added 25 ml. of ethyl acetate and 30 ml. of water and the mixture is stirred thoroughly. The crystalline solid thus obtained is filtered and air dried to give 2.75 g (65.2 per cent yield) of product, which decomposes above 160°C. NMR (DMSO-D6) ppm (δ), 1.74 (s, 3,3-CH3), 3.38 (ABq, δ 0.45 ppm, J 9 cps, 2--CH2), 4.92 (s, 1, 4H), 5.0 (d, 1, 6H), 5.34 (d, 1, 7H), 5.51 (s, 2, CO2CH2 ), 8.05 (ABq, δ 0.525 ppm, J 5 cps, p-NO2 --C6H4).

Workup

  1. stirringthe solution is further stirred for 1 hour
  2. customevaporated
  3. additionTo the residue are added 25 ml
  4. stirringof water and the mixture is stirred thoroughly
  5. customThe crystalline solid thus obtained
  6. filtrationis filtered
  7. customair dried
  8. customto give
  9. custom2.75 g (65.2 per cent yield) of product, which
  10. customdecomposes above 160°C

Sources & evidence

ORD record
ord-d0a1893b344a4676ae708868d7a22402
Source dataset
uspto-grants-1976_01
Patent number
US03932398

Reaction notes

Loading…