HCID 131724668, compound → HCID 118369870, compound

HRID 2417159Notes

Reaction equation

HRID 2417159 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C:2]([C:5]([NH:7][C@H:8]([C:16]([N:18]1[CH2:29][CH2:28][CH2:27][C@@H:19]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6])([CH3:4])[CH3:3]>C(O)(=O)C.[Pd]>[NH2:1][C:2]([C:5]([NH:7][C@H:8]([C:16]([N:18]1[CH2:29][CH2:28][CH2:27][C@@H:19]1[C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 131724668HCID 131724668, compound

Product 1

HCID 118369870HCID 118369870, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Z-Aib-L-Phe-D-Pro-OtBu (1.23 g, 2.28 mmol) was catalytically hydrogenated with Pd-C in acetic acid to remove the Z-group. After the reaction was continued for 10 hours, Pd-C was filtered off and acetic acid was concentrated. The residue was neutralized with 4% NaHCO3 and extracted into ethyl acetate. The extract was dried over Na2CO3 and concentrated to yield 0.726 g (1.80 mmol; 79%) of the titled compound.

Workup

  1. customto remove the Z-group
  2. filtrationPd-C was filtered off
  3. concentrationacetic acid was concentrated
  4. extractionextracted into ethyl acetate
  5. dry with materialThe extract was dried over Na2CO3
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4bb2daffb197425caf8811a0009a58a4
Source dataset
uspto-grants-2004_11
Patent number
US06825317B2

Reaction notes

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