HCID 70576524, compound → HCID 53661776, compound

HRID 1856000Notes

Reaction equation

HRID 1856000 reaction equation
[CH3:1][NH:2][C:3]([O:5][CH:6]1[CH2:10][NH:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7]1)=[O:4].[H][H]>[C].[Pd].CO.O>[CH3:1][NH:2][C:3]([O:5][C@H:6]1[CH2:10][NH:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7]1)=[O:4]

Participants

5

Reactant 2

HCID 70576524HCID 70576524, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53661776HCID 53661776, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 2.7 g. (0.0084 mole) of trans-N-carbobenzyloxy]-4-[[(methylamino)carbonyl]oxy]-L-proline in 100 ml. of methanol-water (2:1) is treated with 1 g. of 5% palladium-carbon and 45 lb. of hydrogen and shaken on a Parr hydrogenator for 6 hours. The catalyst is filtered off under nitrogen, washed with methanol and the combined filtrates are evaporated, finally at 0.1-0.2 mm, to give 1.5 g. (96%) of a residue which gradually crystallizes to give trans-4-[[(methylamino)carbonyl]oxy]-L-proline as a greyish solid; m.p. 213°-215° (dec.), preceded by gradual darkening and sintering. [α]D26 -12° (c, 0.25% in 1:3 ethanol-methanol).

Workup

  1. filtrationThe catalyst is filtered off under nitrogen
  2. washwashed with methanol
  3. customthe combined filtrates are evaporated, finally at 0.1-0.2 mm
  4. customto give 1.5 g
  5. custom(96%) of a residue which gradually crystallizes

Sources & evidence

ORD record
ord-1345453fc9a14a24a8a019b2101084ce
Source dataset
uspto-grants-1980_08
Patent number
US04217359

Reaction notes

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