2-Iodoxybenzoic acid → HCID 131722488, compound

HRID 323551Notes

Reaction equation

HRID 323551 reaction equation
[NH:1]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:31][C@H:32]([CH2:37][OH:38])[CH2:33][CH2:34][S:35][CH3:36].I(C1C=CC=CC=1C(O)=O)(=O)=O>CS(C)=O>[NH:1]([C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:31][C@H:32]([CH:37]=[O:38])[CH2:33][CH2:34][S:35][CH3:36]

Participants

4

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 131722489HCID 131722489, compound

Product 1

HCID 131722488HCID 131722488, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

CBZ-L-Leu-L-Phe-L-methioninol (sulfoxide) (1.38 g, 2.53 mmol) was dissolved in DMSO. o-Iodoxybenzoic acid (2.12 g, 7.59 mmol) was added, requiring a few minutes of stirring at room temperature to dissolve. After three hours, the DMSO was removed under reduced pressure. The residue was twice diluted with CH2Cl2, and the solvent was evaporated to remove any residual DMSO. The residue was diluted with a minimum of acetone, and the white precipitate was filtered off. The filtrate was concentrated to near dryness and dissolved in EtOAc, which produced more of the white precipitate, which was again filtered off. The filtrate was washed with a 10% Na2S2O3/10% NaHCO3 solution, water, and brine before drying over Na2SO4. Upon removal of the organic solvent, the residue was twice taken up in benzene and evaporated to remove any residual water, giving 0.98 g (71%) of a white glassy solid which was used immediately without further purification: 1H NMR (DMSO-d6) δ 6 0.81 (m, 6H), 1.30 (m, 2H), 1.50 (m, 1H), 1.97 (m, 1H), 2.48 (s, 3H), 2.55-3.27 (m, 5H), 3.70 (m, 1H), 4.47 (m, 1H), 4.71 (m, 1H), 5.00 (s, 2H), 7.20-7.40 (m, 10H), 7.93 (m, 1H), 8.08 (m, 1H), 8.51 (m, 1H), 9.22 (s, 1H); (M+H) 544.

Workup

  1. waitrequiring a few minutes
  2. dissolutionto dissolve
  3. customthe DMSO was removed under reduced pressure
  4. additionThe residue was twice diluted with CH2Cl2
  5. customthe solvent was evaporated
  6. customto remove any residual DMSO
  7. additionThe residue was diluted with a minimum of acetone
  8. filtrationthe white precipitate was filtered off
  9. concentrationThe filtrate was concentrated
  10. dissolutiondissolved in EtOAc
  11. customwhich produced more of the white precipitate, which
  12. filtrationwas again filtered off
  13. washThe filtrate was washed with a 10% Na2S2O3/10% NaHCO3 solution, water, and brine
  14. dry with materialbefore drying over Na2SO4
  15. customUpon removal of the organic solvent
  16. customevaporated
  17. customto remove any residual water

Sources & evidence

ORD record
ord-06ee7bdffd004e4fb6749031c1711ac9
Source dataset
uspto-grants-2001_04
Patent number
US06214799B1

Reaction notes

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