Sodium Bisulfate → HCID 25989296, compound

HRID 276730Notes

Reaction equation

HRID 276730 reaction equation
C(C1C=C(SCOC[C@@H]([NH:17][C:18](=[O:44])[C@H:19]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39](C)[CH:38]=2)[NH:20][C:21](=[O:35])[CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)C#N)C=CC=1)(O)=O.S([O-])(O[O-])(=O)=O.[K+].[K+].OS([O-])(=O)=O.[Na+]>CC(C)=O.O>[C:29]1([CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:21]([NH:20][C@H:19]([C:18]([NH2:17])=[O:44])[CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:35])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 516919Sodium BisulfateHCID 10313463Potassium peroxymonosulphateHCID 22951547HCID 22951547, compound

Product 1

HCID 25989296HCID 25989296, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-[2-[(3-carboxyphenyl)thiomethoxy]-1(S)-cyanoethyl]-3-methyl-Nα-(2,2-diphenylacetyl)-L-phenylalaninamide (89 mg, 0.15 mmol) in acetone (5 mL) is added a solution of potassium peroxymonosulfate (Oxone®, 0.11 g, 0.18 mmol) in water (5 mL) at 0° C., and the solution is stirred at 0° C. for 40 minutes. 5% NaHSO4 (10 mL) is added, and the cloudy suspension is filtered. The solid is washed with water (50 mL), dried in vacuo, and then recrystalized (CH2Cl2, Et2O) to yield N-[2-[(3-carboxyphenyl)methanesulfinyl]-1(S)-cyanoethyl]-3-methyl-Nα-(2,2-diphenylacetyl-L-phenylalaninamide product, as a white solid, m.p. 170-171° C.

Workup

  1. filtrationthe cloudy suspension is filtered
  2. washThe solid is washed with water (50 mL)
  3. customdried in vacuo
  4. customrecrystalized (CH2Cl2, Et2O)

Sources & evidence

ORD record
ord-64458f03c00c4fbcb3985f02450c776d
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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