HCID 22884166, compound → HCID 67629231, compound

HRID 1598480Notes

Reaction equation

HRID 1598480 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:10]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25]C(OC(C)(C)C)=O)[CH2:9]1)C1C=CC=CC=1.[H][H]>[Pd].CO>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]1[CH2:21][CH2:22][CH2:23][CH:24]([NH2:25])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:15])([CH3:18])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 22884166HCID 22884166, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67629231HCID 67629231, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared according to the procedure described in Example 2, Step C except using 4-benzyl-1-tert-butoxycarbonyl-2(S)-(4-tert-butoxycarbonylaminobutyl)-piperazine (3.74 g, 8.36 mmol), 10% palladium on carbon (0.50 g) in methanol (50 mL) for 48 h at 60 psi hydrogen. The title compound (Rf 0.3 in 5% methanol in chloroform) was obtained as an oil (3.14 g). NMR (300 MHz, CDCl3) d 4.59 (1H, m), 4.00 (1H, m), 3.83 (1H, br d J=12 Hz), 3.12 (2H, m), 2.90 (4H, m), 2.70 (1H, dt, J=4, 13 Hz), 1.0-1.9 (25H, m).

Workup

  1. customThe title compound was prepared
  2. customfor 48 h

Sources & evidence

ORD record
ord-5064b1a740984c50b25b3b4c222499cf
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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