HCID 13686730, compound → HCID 13686732, compound

HRID 652470Notes

Reaction equation

HRID 652470 reaction equation
C([O:8][C:9](=[O:48])[C@H:10]([CH2:33][CH2:34][CH2:35][CH2:36][NH:37]C(OCC1C=CC=CC=1)=O)[NH:11][C:12](=[O:32])[CH2:13][CH2:14][C@H:15]([C:29](=[O:31])[NH2:30])[NH:16][C:17](=[O:28])[C@H:18]([CH3:27])[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[C:23]([O:22][C:20]([NH:19][C@H:18]([C:17]([NH:16][C@@H:15]([C:29](=[O:31])[NH2:30])[CH2:14][CH2:13][C:12]([NH:11][C@H:10]([C:9]([OH:48])=[O:8])[CH2:33][CH2:34][CH2:35][CH2:36][NH2:37])=[O:32])=[O:28])[CH3:27])=[O:21])([CH3:24])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 13686730HCID 13686730, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13686732HCID 13686732, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

In 40 ml of acetic acid was dissolved 4.00 g of Nα -(t-butyloxycarbonyl-alanyl-D-isoglutaminyl)-Nε -benzyloxycarbonyl-lysine benzyl ester, and the solution was hydrogenolyzed in the presence of palladium-on-carbon in a hydrogen stream at room temperature. The catalyst was removed by filtration, and the filtrate was concentrated. To the residue was added diethyl ether, and the precipitated powder was recrystallized from methanoldiethyl ether to obtain 2.37 g of Nα -(t-butyloxycarbonylalanyl-D-isoglutaminyl)-lysine.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. additionTo the residue was added diethyl ether
  4. customthe precipitated powder was recrystallized from methanoldiethyl ether

Sources & evidence

ORD record
ord-73a228cf9b0f493196b3f05e24f14cb1
Source dataset
uspto-grants-1987_06
Patent number
US04672106

Reaction notes

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