HCID 86747491, compound → HCID 54055012, compound

HRID 1198070Notes

Reaction equation

HRID 1198070 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([CH3:43])([NH:29][C:30]([O:32][CH:33]2[CH:40]3[CH2:41][CH:36]4[CH2:37][CH:38]([CH2:42][CH:34]2[CH2:35]4)[CH2:39]3)=[O:31])[C:12]([NH:14][CH2:15][CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[O:20])=[O:13])=[CH:2]1>[Pd].C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([CH3:43])([NH:29][C:30]([O:32][CH:33]2[CH:40]3[CH2:39][CH:38]4[CH2:37][CH:36]([CH2:35][CH:34]2[CH2:42]4)[CH2:41]3)=[O:31])[C:12]([NH:14][CH2:15][CH:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[O:13])=[CH:2]1

Participants

4

Reactant 1

HCID 86747491HCID 86747491, compound

Product 1

HCID 54055012HCID 54055012, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The ester from Step 3 (0.228 g, 0.39 mmol) wa hydrogenated over 10% palladium on charcoal in absolute ethanol (50 mL) under an atmosphere of hydrogen at 45 psi and 30° C. for 7 hours. The catalyst was filtered and the solvent removed in vacuo, giving the product (0.217 g, 95%) as a white solid, mp 69°-76° C.; IR (film) 1714 and 1660 cm-1 ; NMR (CDCl3) 1.48-1.93 (19H, m), 2.11.varies.2.17 (2H, m), 2.50-2.68 (1H, m), 3.14-3.65 (7H, m), 4.74 (1H, s), 5.11 (1H, bs), 6.00-6.13 (1H, m), 6.90-6.99 (3H, m), 7.08-7.22 (5H, m), 7.35 (1H, d, J 8.0 Hz), 7.54-7.58 (1H, m), 8.28 (1H, bs); Anal. (C35H43N3O5.0.5H2O) C, H. N.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-25c0dfe8dbb44a39a523b6921cf12e67
Source dataset
uspto-grants-1994_01
Patent number
US05278316

Reaction notes

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