3,4,5-Trimethoxybenzaldehyde → HCID 54001398, compound

HRID 903459Notes

Reaction equation

HRID 903459 reaction equation
COC1C=C(C=C(OC)C=1OC)C=O.COC1C=C(C=C(OC)C=1OC)C(CCC(O)=O)=O.N1CCC[C@H]1C(O)=O.[CH3:42][O:43][C:44]1[CH:45]=[C:46]([CH:61]=[C:62]([O:66][CH3:67])[C:63]=1[O:64][CH3:65])[C:47]([CH2:49][CH2:50][C:51]([N:53]1[CH2:60][CH2:59][CH2:58][C@H:54]1[C:55]([OH:57])=[O:56])=[O:52])=[O:48].[Br:68]Br>C(O)(=O)C>[Br:68][CH:49]([C:47](=[O:48])[C:46]1[CH:61]=[C:62]([O:66][CH3:67])[C:63]([O:64][CH3:65])=[C:44]([O:43][CH3:42])[CH:45]=1)[CH2:50][C:51]([N:53]1[CH2:60][CH2:59][CH2:58][C@H:54]1[C:55]([OH:57])=[O:56])=[O:52]

Participants

7

Reactant 5

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 24408BromineHCID 145742L-ProlineHCID 2900944-oxo-4-(3,4,5-trimethoxyphenyl)butanoic acidHCID 54468486HCID 54468486, compound

Product 1

HCID 54001398HCID 54001398, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

As described in Example 52, 3,4,5-trimethoxybenzaldehyde is converted to 3-(3,4,5-trimethoxybenzoyl)propionic acid. The preceding compound is converted to the hydroxysuccinimide ester as described in Example 15 and coupled to L-proline as described in Example 16. The 1-[3-(3,4,5-trimethoxybenzoyl)propionyl]-L-proline is reacted with bromine in acetic acid as in Example 20 to give 1-[3-bromo-3-(3,4,5-trimethoxybenzoyl)propionyl]-L-proline. The preciding compound is reacted with potassium thioacetate in ethanol-water as in Example 21 to give the product of the Example as a glass.

Sources & evidence

ORD record
ord-ad7c7ef94e024921a903ffe6faf92334
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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