Hydrochloric Acid → HCID 70055004, compound

HRID 345229Notes

Reaction equation

HRID 345229 reaction equation
[CH3:1][C:2]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:3]=1[C:4]([O:6][CH2:7][C:8]([CH2:10][O:11][C:12](=[O:22])[C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21])=[O:9])=[O:5].C([NH:39][C@H:40]([C:48]([NH:50][C@H:51]([C:53]([OH:55])=[O:54])[CH3:52])=[O:49])[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)(OCC1C=CC=CC=1)=O.C(O)C.[ClH:59]>[Pd]>[ClH:59].[CH3:19][C:18]1[CH:17]=[C:16]([CH3:20])[CH:15]=[C:14]([CH3:21])[C:13]=1[C:12]([O:11][CH2:10][C:8]([CH2:7][O:6][C:4](=[O:5])[C:3]1[C:23]([CH3:28])=[CH:24][C:25]([CH3:27])=[CH:26][C:2]=1[CH3:1])=[O:9])=[O:22].[NH2:39][C@H:40]([C:48]([NH:50][C@H:51]([C:53]([OH:55])=[O:54])[CH3:52])=[O:49])[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 70054152HCID 70054152, compound

Product 1

HCID 70055004HCID 70055004, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a mixture of N-CBZ-L-phenylalanyl-L-alanine 2,4,6-trimethylbenzoyloxymethyl ketone (0.38 mmol, 200 mg) in 100 mL of ethanol containing 150 μL (0.75 mmol) of 5 N HCl was added 10% palladium on charcoal (20 mg). This mixture was vigorously stirred under an atmosphere of hydrogen gas for 3 hours, the catalyst was removed by filtration through a bed of Celite, and the filtrate was rotary evaporated under reduced pressure. The residue was then precipitated from ethanol-ethyl ether, washed with ethyl ether, and dried at high vacuum to quantitatively afford the product as a powder, m.p. 123°-126° C.

Workup

  1. customthe catalyst was removed by filtration through a bed of Celite
  2. customthe filtrate was rotary evaporated under reduced pressure
  3. customThe residue was then precipitated from ethanol-ethyl ether
  4. washwashed with ethyl ether
  5. customdried at high vacuum

Sources & evidence

ORD record
ord-6a0a7b1ed6ad4679befaf35b0222ca5e
Source dataset
uspto-grants-1991_10
Patent number
US05055451

Reaction notes

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