Methane → HCID 9849953, compound

HRID 975994Notes

Reaction equation

HRID 975994 reaction equation
C.[C:2]([O:6][C:7]([C@@H:9]1[CH2:13][S:12][C@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[N:10]1[C:21](=[O:45])[CH2:22][NH:23][C:24](=[O:44])[NH:25][C:26]1[CH:27]=[C:28]([CH:32]([CH3:43])[C:33]([O:35]CC2C=CC=CC=2)=[O:34])[CH:29]=[CH:30][CH:31]=1)=[O:8])([CH3:5])([CH3:4])[CH3:3]>C(OCC)(=O)C.[OH-].[Na+]>[C:2]([O:6][C:7]([C@@H:9]1[CH2:13][S:12][C@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[N:10]1[C:21](=[O:45])[CH2:22][NH:23][C:24](=[O:44])[NH:25][C:26]1[CH:27]=[C:28]([CH:32]([CH3:43])[C:33]([OH:35])=[O:34])[CH:29]=[CH:30][CH:31]=1)=[O:8])([CH3:4])([CH3:3])[CH3:5]

Participants

5

Reactant 2

HCID 297MethaneHCID 54292755HCID 54292755, compound

Product 1

HCID 9849953HCID 9849953, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

0.1 g of 10% palladinised charcoal is added to a solution of 0.35 g of benzyl 2-{3-{3-{2-[(2R,4R)-4-tert-butoxycarbonyl-2-(2-fluorophenyl)-3-thiazolidinyl]-2-oxoethyl}ureido}phenyl}propionate (B form) in 40 cm3 of ethyl acetate. The suspension is stirred for 48 hours at a temperature in the vicinity of 25° C. under a hydrogen atmosphere (100 kPa). The catalyst is then separated by filtration and the filtrate is concentrated to dryness under reduced pressure at 40° C. The residue obtained is dissolved in 10 cm3 of 0.1N aqueous sodium hydroxide solution and washed with 2 times 10 cm3 of ethyl ether. The aqueous phase is brought to a pH of 2 by addition of a 1N aqueous sulphuric acid solution. The product precipitated is separated by filtration, is washed with 2 times 10 cm3 of water and dried in air. 0.12 g of 2-{3-{3-{2-[(2R,4R)-4-tert-butoxycarbonyl-2-(2-fluorophenyl)-3-thiazolidinyl]-2-oxoethyl}ureido}-phenyl}propionic acid (B form), melting at 126° C., is thus obtained.

Workup

  1. customThe catalyst is then separated by filtration
  2. concentrationthe filtrate is concentrated to dryness under reduced pressure at 40° C
  3. customThe residue obtained
  4. washwashed with 2 times 10 cm3 of ethyl ether
  5. additionThe aqueous phase is brought to a pH of 2 by addition of a 1N aqueous sulphuric acid solution
  6. customThe product precipitated
  7. customis separated by filtration
  8. washis washed with 2 times 10 cm3 of water
  9. customdried in air

Sources & evidence

ORD record
ord-e79fd4346a5e4b25b42be141fe4b2709
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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