Acetonitrile → HCID 5280190, compound

HRID 899367Notes

Reaction equation

HRID 899367 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:36])[C:16]([C:18]2[C:26]3[C:21](=[C:22]([CH:29]4[CH:33]=[CH:32][C:31](=[C:34]=[O:35])[O:30]4)[N:23]=[CH:24][C:25]=3[O:27][CH3:28])[NH:20][CH:19]=2)=[O:17])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-:37]Cl=O.[Na+].CC#N>O>[C:1]([N:9]1[CH2:10][CH2:11][N:12]([C:15](=[O:36])[C:16]([C:18]2[C:26]3[C:21](=[C:22]([C:29]4[O:30][C:31]([C:34]([OH:37])=[O:35])=[CH:32][CH:33]=4)[N:23]=[CH:24][C:25]=3[O:27][CH3:28])[NH:20][CH:19]=2)=[O:17])[CH2:13][CH2:14]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 23668197Sodium ChloriteHCID 87288404HCID 87288404, compound

Product 1

HCID 5280190HCID 5280190, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the compound of Example 85 (19 mg), NaClO2 (9.2 mg) in a mixed solution of CH3CN (3 mL) and water (0.5 mL) was stirred at room temperature for 24 hours. After the reaction was quenched by 1N NaOH solution (1 ml), the mixture was extracted with diethyl ether (3×10 mL). The aqueous phase was acidified with 1N HCl to give a yellow solid precipitate (5 mg) which was the product shown. MS m/z: (M+H)+ Calc'd for C26H23N6O7: 503.16; found 503.19. HPLC retention time: 1.37 minutes (column A).

Workup

  1. customAfter the reaction was quenched by 1N NaOH solution (1 ml)
  2. extractionthe mixture was extracted with diethyl ether (3×10 mL)

Sources & evidence

ORD record
ord-075b5437486a4b21a2416eb1486c0bd5
Source dataset
uspto-grants-2008_04
Patent number
US07354924B2

Reaction notes

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