HCID 18697866, compound → HCID 18697752, compound

HRID 2289565Notes

Reaction equation

HRID 2289565 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:35]=[CH:34][C:12]([C:13]([C:15]2[N:16]=[N:17][N:18]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:19]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:14])=[C:11]([N+:36]([O-])=O)[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(NC1C=CC(C(C2N(CC3C=CC(OC)=CC=3)N=NC=2C(OCC)=O)=O)=C([N+]([O-])=O)C=1)=O)(C)(C)C>C(OCC)(=O)C.[Pd]>[NH2:36][C:11]1[CH:10]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH:35]=[CH:34][C:12]=1[C:13]([C:15]1[N:16]=[N:17][N:18]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)[C:19]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:14]

Participants

5

Reactant 2

HCID 18697866HCID 18697866, compoundHCID 18697913HCID 18697913, compound

Product 1

HCID 18697752HCID 18697752, compoundYield 26.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the 1:1 mixture (872 mg) of ethyl 4-(4-t-butoxycarbonylamino-2-nitrobenzoyl)-1-(4-methoxybenzyl)-1,2,3-triazole-5-carboxylate and ethyl 5-(4-t-butoxycarbonylamino-2-nitrobenzoyl)-1-(4-methoxybenzyl)-1,2,3-triazole-4-carboxylate, prepared in the step (b), in ethyl acetate (20 ml) was added 10% palladium on carbon (30 mg). The mixture was stirred under a hydrogen atmosphere overnight and filtered. The filtrate was concentrated under reduced pressure, and the resulting oil was purified by column chromatography on silica gel (toluene:ethyl acetate=2:1) to give ethyl 4-(2-amino-4-t-butoxycarbonylaminobenzoyl)-1-(4-methoxybenzyl)-1,2,3-triazole-5-carboxylate (c-1: less polar component (LP)) (217 mg) and a mixture (219 mg) of the compound c-1 and ethyl 5-(2-amino-4-t-butoxycarbonylaminobenzoyl)-1-(4-methoxybenzyl)-1,2,3-triazole-4-carboxylate (c-2: more polar component (MP)) (219 mg). c-1 (LP):

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe resulting oil was purified by column chromatography on silica gel (toluene:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-226af01a2e784774ba986978c17cc0cc
Source dataset
uspto-grants-2000_07
Patent number
US06093714

Reaction notes

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