Trifluoroacetic acid → HCID 53685458, compound

HRID 851441Notes

Reaction equation

HRID 851441 reaction equation
[CH3:1][C:2]([CH3:49])([CH3:48])[C:3](=[O:47])[O:4][CH2:5][O:6][P:7]([CH2:19][C:20]([N:22]1[C@H:30]([C:31]([O:33]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:32])[CH2:29][C:24]2([S:28][CH2:27][CH2:26][S:25]2)[CH2:23]1)=[O:21])([CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:8].FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]([CH3:49])([CH3:48])[C:3](=[O:47])[O:4][CH2:5][O:6][P:7]([CH2:19][C:20]([N:22]1[C@H:30]([C:31]([OH:33])=[O:32])[CH2:29][C:24]2([S:25][CH2:26][CH2:27][S:28]2)[CH2:23]1)=[O:21])([CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86738448HCID 86738448, compound

Product 1

HCID 53685458HCID 53685458, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-7-[[[(2,2-Dimethyl-1-oxopropoxy)methoxy]-(4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester (2.4 g) in dry dichloromethane is treated with 3.0 ml of trifluoroacetic acid under argon at room temperature. After 1 hour, the trifluoroacetic acid and dichloromethane are removed in vacuo and the resulting oil partioned between ethyl acetate and water. The layers are separated and the organic phase is washed with brine, dried (MgSO4) and evaporated. The residue (4.0 g) is chromatographed on 130 g of silica eluting with dichloromethane/acetic acid/methanol (18:1:1) to give (after azeotropic removal of acetic acid with toluene) 1.5 g of the title compound.

Workup

  1. customthe trifluoroacetic acid and dichloromethane are removed in vacuo
  2. customThe layers are separated
  3. washthe organic phase is washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue (4.0 g) is chromatographed on 130 g of silica eluting with dichloromethane/acetic acid/methanol (18:1:1)
  7. customto give
  8. custom(after azeotropic removal of acetic acid with toluene) 1.5 g of the title compound

Sources & evidence

ORD record
ord-11baf89de6b949df8626eea9ce5487a0
Source dataset
uspto-grants-1983_05
Patent number
US04384123

Reaction notes

Loading…