Methanol → HCID 9957833, compound

HRID 1781304Notes

Reaction equation

HRID 1781304 reaction equation
CO.[C:3]([O:7][C:8]([C@@H:10]1[CH2:14][S:13][CH:12]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[N:11]1[C:21](=[O:44])[CH2:22][NH:23][C:24](=[O:43])[NH:25][C:26]1[CH:27]=[C:28]([CH2:32][C:33]([O:35]CC2C=CC=CC=2)=[O:34])[CH:29]=[CH:30][CH:31]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C([O-])=O.[NH4+]>[Pd].[OH-].[Na+]>[C:3]([O:7][C:8]([C@@H:10]1[CH2:14][S:13][CH:12]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[N:11]1[C:21](=[O:44])[CH2:22][NH:23][C:24](=[O:43])[NH:25][C:26]1[CH:27]=[C:28]([CH2:32][C:33]([OH:35])=[O:34])[CH:29]=[CH:30][CH:31]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 15199142HCID 15199142, compound

Product 1

HCID 9957833HCID 9957833, compoundYield 58.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

30 cm3 of methanol are added slowly under an inert atmosphere into a round-bottomed flask containing 2.0 g of benzyl (4R) -3-{3- [2- (4-tert-butoxycarbonyl-2-cyclohexyl-3-thiazolidinyl)-2-oxoethyl]-ureido}phenyl-acetate (isomer A), 1.7 g of ammonium formate and 2.0 g of palladium on charcoal (10% Pd). The reaction medium is heated to reflux for 2 hours and then cooled to a temperature in the region of 25° C. The catalyst is separated by filtration and the filtrate is concentrated to dryness under reduced pressure at 40° C. The residue obtained is dissolved in 25 cm3 of 0.1N aqueous sodium hydroxide solution and washed with twice 10 cm3 of diethyl ether. The aqueous phase is brought to pH 2 by adding 1N aqueous sulphuric acid solution. The precipitated product is separated by filtration, washed with twice 10 cm3 of water and dried in the air. 1.0 g of (4R) -3-{3- [2- (4-tert-butoxycarbonyl-2-cyclohexyl-3-thiazolidinyl)-2-oxoethyl]ureido}phenylacetic acid (isomer A), melting point 115° C., is thereby obtained; [α]D25 =-32.9°±1.2° (C %=1.2; DMF).

Workup

  1. temperatureThe reaction medium is heated
  2. temperatureto reflux for 2 hours
  3. customThe catalyst is separated by filtration
  4. concentrationthe filtrate is concentrated to dryness under reduced pressure at 40° C
  5. customThe residue obtained
  6. washwashed with twice 10 cm3 of diethyl ether
  7. additionby adding 1N aqueous sulphuric acid solution
  8. customThe precipitated product is separated by filtration
  9. washwashed with twice 10 cm3 of water
  10. customdried in the air

Sources & evidence

ORD record
ord-d58c7e03f08a4b1398a99627fe4be9d6
Source dataset
uspto-grants-1997_05
Patent number
US05633270

Reaction notes

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