Triethylamine → Glyoxylic Acid

HRID 1972143Notes

Reaction equation

HRID 1972143 reaction equation
[CH3:1][C:2]([C:5]1[CH:33]=[C:32]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:30](=[O:31])[C:7](=[CH:8][NH:9][CH2:10][CH2:11][CH2:12][NH:13][CH:14]=[C:15]2[C:20](=[O:21])[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][C:17]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:16]2)[CH:6]=1)([CH3:4])[CH3:3].O.[C:39]([OH:43])(=[O:42])[CH:40]=[O:41].C(N(CC)CC)C>CO.[Pd]>[CH3:29][C:26]([C:17]1[CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20](=[O:21])[C:15](=[CH:14][NH:13][CH2:12][CH2:11][CH2:10][NH:9][CH:8]=[C:7]2[C:30](=[O:31])[C:32]([C:34]([CH3:35])([CH3:36])[CH3:37])=[CH:33][C:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[CH:6]2)[CH:16]=1)([CH3:27])[CH3:28].[C:39]([OH:43])(=[O:42])[CH:40]=[O:41]

Participants

7

Reactant 3

HCID 8471Triethylamine2×HCID 15620607Glyoxylic acid, monohydrateHCID 178441011HCID 178441011, compound

Product 2

HCID 760Glyoxylic AcidHCID 178441011HCID 178441011, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

The salan compound obtained as described above in 2.1. (3 g, 0.01 mol) was qualitatively transferred to an autoclave containing methanol (100 ml), Pd/C (0.05 g) and the mixture of glyoxylic acid monohydrate (2.8 g, 0.03 mol) with triethylamine (4.0 g, 0.04 mol) in methanol (40 ml) was added to obtain a final molar ratio 1:3:4 (salan:glyoxylic acid:triethylamine). The air remaining over the reaction mixture was removed using the flow of argon stream.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-2ef77ce3fac540cf8450388dfab14c89
Source dataset
uspto-grants-2013_04
Patent number
US08431734B2

Reaction notes

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