Trifluoroacetic acid → HCID 18738807, compound

HRID 1934746Notes

Reaction equation

HRID 1934746 reaction equation
[C:1]([N:9]1[C:13]2([CH2:18][CH2:17][CH:16]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=3)=[O:20])[CH2:15][CH2:14]2)[S:12][CH2:11][C@H:10]1[C:31]([O:33]C(C)(C)C)=[O:32])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([N:9]1[C:13]2([CH2:14][CH2:15][CH:16]([C:19]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:26][CH:27]=3)=[O:20])[CH2:17][CH2:18]2)[S:12][CH2:11][C@H:10]1[C:31]([OH:33])=[O:32])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86758064HCID 86758064, compound

Product 1

HCID 18738807HCID 18738807, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 7 ml of methylene chloride was dissolved 0.35 g of tert-butyl (3R)-4-benzoyl-8-[(4-isopropylanilino)-carbonyl]-1-thia-4-azaspiro[4.5]-decane-3-carboxylate. After adding 1.8 ml of trifluoroacetic acid at 0-5° C., the resulting mixture was stirred at ambient temperature for 6 hours. After distilling off the solvent under reduced pressure, the residue was several times subjected to an azeotropic distillation treatment together with toluene and then purified by column chromatography [eluent: chloroform:ethanol=20:1]. The residue was treated with ethyl ether, and the deposited crystal was collected by filtration to obtain 0.12 g of (3R)-4-benzoyl-8-[(4-isopropylanilino)carbonyl]-1-thia-4-azaspiro[4.5]decane-3-carboxylic acid as a colorless crystalline product.

Workup

  1. distillationAfter distilling off the solvent under reduced pressure
  2. custompurified by column chromatography [eluent: chloroform:ethanol=20:1]
  3. additionThe residue was treated with ethyl ether
  4. filtrationthe deposited crystal was collected by filtration

Sources & evidence

ORD record
ord-8417a44ad4ef4826a02523432b44e1d7
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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