Trifluoroacetic acid → HCID 57018698, compound

HRID 365341Notes

Reaction equation

HRID 365341 reaction equation
[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[C:16]1[N:23]=[C:24]([CH:26]2[CH2:30][O:29]C(C)(C)[O:27]2)[O:25][C:15]1=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[C:16]1[N:23]=[C:24]([CH:26]([OH:27])[CH2:30][OH:29])[O:25][C:15]1=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 56997476HCID 56997476, compound

Product 1

HCID 57018698HCID 57018698, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 200 mg of 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-10-methoxymethyl-oxazolo-[4,5-g]-β-carboline-9-carboxylic acid isopropyl ester in 20 ml of methylene chloride is mixed drop by drop at room temperature with 1 ml of trifluoroacetic acid, and it is stirred at room temperature under protective gas for another 4 hours. The reaction solution is neutralized with the equimolar amount of sodium bicarbonate solution. The precipitated solid product is suctioned off and washed with methylene chloride. After the drying in a vacuum at 50° C., 112 mg of 2-(1,2-dihydroxyethyl)-10-methoxymethyl-oxazolo-[4,5-g]-β-carboline-9-carboxylic acid isopropyl ester with a melting point of 168° C. (decomposition) is obtained.

Workup

  1. washwashed with methylene chloride

Sources & evidence

ORD record
ord-97f77260065f42899658df2a9e1aa01e
Source dataset
uspto-grants-2000_10
Patent number
US06127368

Reaction notes

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