HCID 12083934, compound → 5-Oxo-L-prolyl-L-proline

HRID 1394002Notes

Reaction equation

HRID 1394002 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([N:9]1[CH2:23][CH2:22][CH2:21][C@H:10]1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])=[O:8]>[Pd].CO>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([N:9]1[CH2:23][CH2:22][CH2:21][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8]

Participants

4

Reactant 1

HCID 12083934HCID 12083934, compound

Product 1

HCID 133065895-Oxo-L-prolyl-L-prolineYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

A solution of F2 (8.63 g, 31.34 mmol) and palladium on activated charcoal (10%, 86 mg, 10% w/w) in degassed MeOH (125 mL) was placed in a high pressure Parr reactor and purged with nitrogen gas (2×30 psi). The reaction mixture was sealed under hydrogen (30 psi) and stirred at 23° C. for 4.5 h. The mixture was filtered through a 0.45 □m teflon filter and concentrated at reduced pressure. The residue (6.29 g) was coated in SiO2 and loaded onto the top of a column (LC 5.5×10.0 cm) and eluted with hex:EtOAc 1:2 to yield F1 (4.64 g, 80%) as a white solid. Rf=0.22 (hex:EtOAc 1:1). [α]D20 −92.4 (c 0.12, CHCl3). M.p. 67-69° C.

Workup

  1. custompurged with nitrogen gas (2×30 psi)
  2. customThe reaction mixture was sealed under hydrogen (30 psi)
  3. filtrationThe mixture was filtered through a 0.45 □m teflon
  4. filtrationfilter
  5. concentrationconcentrated at reduced pressure
  6. washeluted with hex

Sources & evidence

ORD record
ord-82c89b9dc36e48edbb2b1b67080d94ef
Source dataset
uspto-grants-2008_03
Patent number
US07348310B2

Reaction notes

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