Trifluoroacetic acid → HCID 13326554, compound

HRID 358530Notes

Reaction equation

HRID 358530 reaction equation
[CH:1]1([CH:7]([O:49][C:50](=[O:53])[CH2:51][CH3:52])[O:8][P:9]([CH2:21][C:22]([N:24]2[C@H:32]([C:33]([O:35]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:34])[CH2:31][C:26]3([S:30][CH2:29][CH2:28][S:27]3)[CH2:25]2)=[O:23])([CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([CH:7]([O:49][C:50](=[O:53])[CH2:51][CH3:52])[O:8][P:9]([CH2:21][C:22]([N:24]2[C@H:32]([C:33]([OH:35])=[O:34])[CH2:31][C:26]3([S:27][CH2:28][CH2:29][S:30]3)[CH2:25]2)=[O:23])([CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86739607HCID 86739607, compound

Product 1

HCID 13326554HCID 13326554, compoundYield 158.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g (1.3 mmol) of (S)-7-[[[cyclohexyl(1-oxopropoxy)methoxy](4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, benzhydryl ester in 10 ml of dichloromethane was stirred, cooled in an ice-bath, treated with 0.3 ml of anisole and 1.0 ml of trifluoroacetic acid (dropwise). After 90 minutes, the solvent and bulk of excess of trifluoroacetic acid were removed on a rotary evaporator and the residue was shaken with 50 ml of ethyl acetate and 20 ml of cold water. The layers were separated (5 ml of ether was added to break up the emulsion) and the organic phase was washed with three 20 ml portions of water. After back-extracting the combined aqueous layers with 25 ml of ethyl acetate, the combined organic layers were washed with 20 ml of saturated sodium chloride, dried (MgSO4), and the solvent evaporated to yield 1.26 g of a syrup. The syrup was purified by chromatography on 60 g of silica gel (60-200 mesh, d=0.37 g/ml) using 40:1:1 dichloromethane:methanol:acetic acid to give 0.74 g of a foam-like solid.

Workup

  1. temperaturecooled in an ice-bath
  2. customthe solvent and bulk of excess of trifluoroacetic acid were removed on a rotary evaporator
  3. customThe layers were separated (5 ml of ether
  4. additionwas added
  5. washwas washed with three 20 ml portions of water
  6. extractionAfter back-extracting the combined aqueous layers with 25 ml of ethyl acetate
  7. washthe combined organic layers were washed with 20 ml of saturated sodium chloride
  8. dry with materialdried (MgSO4)
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-4e4563235f9148ae971d705604a97851
Source dataset
uspto-grants-1984_08
Patent number
US04468519

Reaction notes

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