Methanol → HCID 12718474, compound

HRID 1481664Notes

Reaction equation

HRID 1481664 reaction equation
CO.[NH:3](C(OCC1C=CC=CC=1)=O)[C@H:4]([C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([OH:23])=[O:22])=[O:18])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[H][H]>[Pd].C(O)(=O)C>[NH2:3][C@H:4]([C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([OH:23])=[O:22])=[O:18])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11]

Participants

6

Reactant 3

HCID 887MethanolHCID 14258487HCID 14258487, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12718474HCID 12718474, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

300 ml of absolute methanol, 2 ml of acetic acid, and palladium black were added to 9.68 g (20.26 mmol) of Z-Lys(Boc)-Pro-OH, and hydrogenation was performed in the stream of dry hydrogen at room temperature under 1 atm for 8 hours. Then, the catalyst was filtered off and washed on the filter with methanol. Pooled filtrate was evaporated to dryness. The residue was precipitated with ether from the absolute methanol. Then, it was dried under vacuum, while desiccant was changed several times.

Workup

  1. filtrationThen, the catalyst was filtered off
  2. washwashed on the
  3. filtrationfilter with methanol
  4. customPooled filtrate was evaporated to dryness
  5. customThe residue was precipitated with ether from the absolute methanol
  6. customThen, it was dried under vacuum, while desiccant

Sources & evidence

ORD record
ord-d4e8450b71d84a5cbb3ab29ce015d617
Source dataset
uspto-grants-2016_08
Patent number
US09409947B2

Reaction notes

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