HCID 131723243, compound → HCID 58726315, compound

HRID 2417157Notes

Reaction equation

HRID 2417157 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:10]([N:12]1[CH2:23][CH2:22][CH2:21][C@@H:13]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)(=O)C.[Pd]>[NH2:1][C@H:2]([C:10]([N:12]1[CH2:23][CH2:22][CH2:21][C@@H:13]1[C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 131723243HCID 131723243, compound

Product 1

HCID 58726315HCID 58726315, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Z-L-Phe-D-Pro-OtBu (1.403 g, 3.1 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 0.853 g (86%) 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-859ec2e9cb8047d8a9b03043f747e390
Source dataset
uspto-grants-2004_11
Patent number
US06825317B2

Reaction notes

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