HCID 86749922, compound → HCID 18659920, compound

HRID 864784Notes

Reaction equation

HRID 864784 reaction equation
C([O:8][C:9](=[O:49])[C@H:10]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[NH:11][C:12](=[O:41])[C@H:13]([CH2:30][C:31](=[O:40])[O:32]CC1C=CC=CC=1)[NH:14][C:15](=[O:29])[CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[N:26]1[CH:27]=[CH:28][C:23]([N:20]2[CH2:19][CH2:18][N:17]([CH2:16][C:15]([NH:14][C@H:13]([C:12]([NH:11][C@H:10]([C:9]([OH:49])=[O:8])[CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)=[O:41])[CH2:30][C:31](=[O:32])[OH:40])=[O:29])[CH2:22][CH2:21]2)=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 86749922HCID 86749922, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18659920HCID 18659920, compoundYield 40.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of O-benzyl-N-[O-benzyl-N-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]-L-aspartyl]-L-phenylalanine (0.92 g) in methanol (125 ml) under argon was added 10% Pd on C (0.45 g). The mixture was covered with a blanket of hydrogen and stirred at room temperature until deprotection was complete. The catalyst was filtered off through a pad of kieselguhr and the filtrate was evaporated to dryness. The resultant white solid was dissolved in water and lyophilised overnight to yield the title compound (274 mg) as a white solid: m.p. 153° C. (dec.); NMR (d6DMSO+CD3CO2D) δ2.65 (6H, m), 3.02 (4H, m), 3.63 (4H, m), 4.44 (1H, m), 4.67 (1H, m), 7.13 (2H, d), 7.23 (5H, m), 8.22 (2H, d); m/Z 484 (M+H)+ ; calculated for C24H29N5O6. m/Z 484 (M+H)+ ; amino acid analysis: found; Asp, 1.00; Phe 0.99; requires; Asp, 1.00; Phe, 1.00.

Workup

  1. filtrationThe catalyst was filtered off through a pad of kieselguhr
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe resultant white solid was dissolved in water

Sources & evidence

ORD record
ord-639a1f9d89d8427ebc29d51bd415c53c
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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