Ammonia → HCID 15132288, compound

HRID 1742365Notes

Reaction equation

HRID 1742365 reaction equation
[NH3:1].[CH3:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:35])[NH:11][CH:12]([C:18]([N:20]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])[CH2:13][C:14]([O:16]C)=O)[CH:6]=[CH:7][CH:8]=1>CO>[CH3:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:35])[NH:11][CH:12]([CH2:13][C:14]([NH2:1])=[O:16])[C:18]([N:20]([CH2:27][C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:19])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 15132284HCID 15132284, compound

Product 1

HCID 15132288HCID 15132288, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stream of ammonia is passed for 11 hours at a temperature in the region of 25° C. into a solution of methyl (RS)-3-[3-(3-methylphenyl)ureido]-N-(tertbutoxycarbonylmethyl)-N-phenylsuccinamate (4.7 g) in methanol (150 cc). The solution is then outgassed with a stream of nitrogen and concentrated under vacuum (2.7 kPa) at 60° C. The residue is crystallised in diethyl ether and the solid extracted with dichloromethane (40 cc). The solution thereby obtained is purified by chromatography on silica (0.063-0.200 mm) (25 g) contained in a column 1.6 cm in diameter [eluent: methylene chloride (1100 cc), then methylene chloride/methanol (98.5:1.5 by volume)], collecting 15-cc fractions. Fractions 80 to 127 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 60° C. After crystallisation in petroleum ether, (RS)-2-[3-(3-methylphenyl)ureido]-N-(tert-butoxycarbonylmethyl)-N-phenylsuccinamide (1.1 g), m.p. 192° C., is obtained.

Workup

  1. concentrationconcentrated under vacuum (2.7 kPa) at 60° C
  2. customThe residue is crystallised in diethyl ether
  3. extractionthe solid extracted with dichloromethane (40 cc)
  4. customThe solution thereby obtained
  5. customis purified by chromatography on silica (0.063-0.200 mm) (25 g)
  6. custommethylene chloride (1100 cc), then methylene chloride/methanol (98.5:1.5 by volume)], collecting 15-cc fractions
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 60° C
  8. customAfter crystallisation in petroleum ether

Sources & evidence

ORD record
ord-7c6f58fb68d847ad88af76bdce37f753
Source dataset
uspto-grants-1994_08
Patent number
US05338760

Reaction notes

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