Sodium Hydroxide → HCID 15132294, compound

HRID 1742366Notes

Reaction equation

HRID 1742366 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:35])[NH:10][CH:11]([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])[CH2:12][CH2:13][C:14]([O:16]C)=[O:15])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>>[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:35])[NH:10][CH:11]([C:18]([N:20]([CH2:27][C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 15132292HCID 15132292, compound

Product 1

HCID 15132294HCID 15132294, compoundYield 31.8%

Procedure

The procedure is as in Example 3, but starting with methyl (RS)-4-[3-(3-methylphenyl)ureido]-N-(tert-butoxycarbonylmethyl)-N-phenylglutaramate (4.7 g) and normal sodium hydroxide (9.7 cc). The product obtained is purified by chromatography on silica (0.063-0.200 mm) (60 g) contained in a column 2.4 cm in diameter [eluent: methylene chloride/methanol (99: 1 by volume) (1000 cc), then methylene chloride/methanol (97:3 by volume)], collecting 25-cc fractions. Fractions 42 to 105 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 60° C. After crystallisation in diethyl ether, (RS)-4-[3-(3-methylphenyl) ureido]-N-(tertbutoxycarbonylmethyl)-N-phenylglutaramic acid (1.45 g), m.p. 191° C., is obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on silica (0.063-0.200 mm) (60 g)
  3. custommethylene chloride/methanol (99: 1 by volume) (1000 cc), then methylene chloride/methanol (97:3 by volume)], collecting 25-cc fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 60° C
  5. customAfter crystallisation in diethyl ether

Sources & evidence

ORD record
ord-47f58e19f92d45b58074724404dc7db4
Source dataset
uspto-grants-1994_08
Patent number
US05338760

Reaction notes

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