HCID 70272683, compound → HCID 70274025, compound

HRID 1870652Notes

Reaction equation

HRID 1870652 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@@H:16]([NH:41][C:42]([NH:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:43])[C:17]([N:19]([C:26]([CH:38]([CH3:40])[CH3:39])([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:27](=[O:29])[NH2:28])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C@@H:16]([NH:41][C:42]([NH:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:43])[C:17]([N:19]([C:26]([CH:38]([CH3:39])[CH3:40])([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:27](=[O:29])[NH2:28])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:18])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 70272683HCID 70272683, compound

Product 1

HCID 70274025HCID 70274025, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of Example 14 (475 mg, 0.723 mmol) and 10% Pd/C (50 mg) in ethanol (30 mL) was stirred under an atmosphere of hydrogen for 2 h after which time a further batch of catalyst (50 mg) was added. After 6 h the solids were removed by filtration through celite to afford the crude titled product as a white foam (380 mg). TLC (3% methanol in methylene chloride) Rf =0.23. 1H NMR (300 MHz, CDCl3) d 0.97 (2×d, J=7.0 Hz, 6H), 2.62 (dd, J=13.0, 6.2 Hz, 1H), 2.97 (dd, J=13.0, 4.1 Hz, 1H), 3.64 (s, 3H), 3.70 (d, J=16.6.0 Hz, 1H), 4.19 (d, J=16.6.0 Hz, 1H) 4.90 (m, 2H), 6.38 (d, J=9.0 Hz, 1H), 6.6-7.6 (m, 20H). C34H36N4O5 requires m/z 580.6838; found 580.6852.

Workup

  1. additionwas added
  2. customAfter 6 h the solids were removed by filtration through celite

Sources & evidence

ORD record
ord-39f328c7881a46d9819d89551fc7c61a
Source dataset
uspto-grants-2000_08
Patent number
US06096885

Reaction notes

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