HCID 22814775, compound → HCID 53661776, compound

HRID 1414070Notes

Reaction equation

HRID 1414070 reaction equation
C([N:11]1[CH2:18][C@H:17]([O:19][C:20]([NH:22][CH3:23])=[O:21])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O.[H][H]>[C].[Pd].CO.O>[CH3:23][NH:22][C:20]([O:19][C@H:17]1[CH2:18][NH:11][C@H:12]([C:13]([OH:15])=[O:14])[CH2:16]1)=[O:21]

Participants

5

Reactant 2

HCID 22814775HCID 22814775, 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-472cda4926904690a05eb5e6fe4e8fee
Source dataset
uspto-grants-1981_02
Patent number
US04252943

Reaction notes

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