Trifluoroacetic acid → HCID 53968774, compound

HRID 1863195Notes

Reaction equation

HRID 1863195 reaction equation
[OH:1][P:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH2:4][CH2:5][C:6]([N:8]1[CH2:19][CH2:18][CH2:17][C@H:9]1[C:10]([O:12]C(C)(C)C)=[O:11])=[O:7])=[O:3].FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[OH:3][P:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH2:4][CH2:5][C:6]([N:8]1[CH2:19][CH2:18][CH2:17][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])=[O:1]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131711629HCID 131711629, compound

Product 1

HCID 53968774HCID 53968774, compound

Procedure

1-[3-(Hydroxyphenylphosphinyl)-1-oxopropyl]-L-proline, 1,1-dimethylethyl ester (1.40 gm., 0.0038 mol.) is dissolved in 20 ml. trifluoroacetic acid and 5ml. anisole and stirred 1 hour. The acid is removed in vacuo and the residue triturated several times with ether/hexane. The residue is taken up in water and the solution washed with ether, millipore filtered and lyophilized. The resulting foam is crystallized from ethyl acetate to give 1-[3-(hydroxyphenylphosphinyl)-1-oxopropyl]-L-proline m.p., 125°-128°, total 300 mg. (25%).

Workup

  1. customThe acid is removed in vacuo
  2. customthe residue triturated several times with ether/hexane
  3. washthe solution washed with ether, millipore
  4. filtrationfiltered
  5. customThe resulting foam is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-048dd09a23db472bad3f6e5a8b1c951e
Source dataset
uspto-grants-1979_09
Patent number
US04168267

Reaction notes

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