N-(N-Acetyl-tyrosinyl-valinyl-pipecolyl)-4-amino-5-benzyloxy-2-oxotetrahydrofuran → N-(N-Acetyl-tyrosinyl-valinyl-pipecolyl)-3-amino-4-oxobutanoic Acid

HRID 2257396Notes

Reaction equation

HRID 2257396 reaction equation
[C:1]([NH:4][C@H:5]([C:14]([NH:16][C@H:17]([C:21]([N:23]1[CH2:45][CH2:44][CH2:43][CH2:42][CH:24]1[C:25]([NH:27][CH:28]1[CH:32]([O:33]CC2C=CC=CC=2)[O:31][C:30](=[O:41])[CH2:29]1)=[O:26])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(=[O:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([NH:4][C@H:5]([C:14]([NH:16][C@H:17]([C:21]([N:23]1[CH2:45][CH2:44][CH2:43][CH2:42][CH:24]1[C:25]([NH:27][CH:28]([CH:32]=[O:33])[CH2:29][C:30]([OH:41])=[O:31])=[O:26])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 66756123N-(N-Acetyl-tyrosinyl-valinyl-pipecolyl)-4-amino-5-benzyloxy-2-oxotetrahydrofuran

Product 1

HCID 86599022N-(N-Acetyl-tyrosinyl-valinyl-pipecolyl)-3-amino-4-oxobutanoic Acid

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 100 mg of N-(N-Acetyl-tyrosinyl-valinyl-pipecolyl)-4-amino-5-benzyloxy-2-oxotetrahydrofuran in 10 ml of methanol was added 60 mg of Pd(OH)2 on carbon and the mixture placed under an atmosphere of hydrogen via a balloon. The mixture was filtered through Celite and concentrated providing a white solid. This crude solid was dissolved in 2 ml of methanol and triturated with diethyl ether affording 26 mg of the title compound.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customproviding a white solid
  4. customtriturated with diethyl ether affording 26 mg of the title compound

Sources & evidence

ORD record
ord-b275d66aa7b14ef8a505099a2b23770c
Source dataset
uspto-grants-1997_08
Patent number
US05656627

Reaction notes

Loading…