Oxalic Acid → HCID 21071605, compound

HRID 1666820Notes

Reaction equation

HRID 1666820 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].CCOC(C)=O.CO.[F:15][C:16]1[CH:17]=[C:18]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[C:21]([CH2:22][CH2:23][NH2:24])=[CH:20][NH:19]2.CCOCC>CO>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[F:15][C:16]1[CH:17]=[C:18]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[C:21]([CH2:22][CH2:23][NH2:24])=[CH:20][NH:19]2

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 3283Diethyl EtherHCID 601383HCID 601383, compoundHCID 21584119Ethylacetate methanol

Product 1

HCID 21071605HCID 21071605, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add oxalic acid (3.91 g, 1.2 eq.) in MeOH dropwise to an EtOAc/MeOH solution of 6-fluoro-5-methoxytryptamine with vigorous stirring. Add Et2O to give a solid and collect the solid by filtration and dry overnight in a vacuum oven at 60° C. to give the title compound: 1H NMR (300 MHz, d6-DMSO): 3.0 (m, 4H), 3.85 (s, 3H), 7.21 (m, 3H), 10.89 (bs, 1H); MS (ES+): m/z 209 (M+H)+; Analysis for C13H15FN2O5: Calcd.: C, 52.3496; H, 5.0690; N, 9.3919. Found: C, 52.06; H, 4.91; N, 9.20.

Workup

  1. customcollect the solid
  2. filtrationby filtration
  3. customdry overnight in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-4967276558394d018455a7c1ff5af38c
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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