Hydrochloric Acid → HCID 49763447, compound

HRID 1182683Notes

Reaction equation

HRID 1182683 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:35])[CH2:15][NH:16][C:17]([C:19]2[N:20]=[C:21]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[S:22][C:23]=2[NH:24][CH2:25][CH2:26][CH2:27][OH:28])=[O:18])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].C(OC1C(OC(=O)C)=C(I)C=CC=1)(=[O:38])C.CC1(C)N([O])C(C)(C)CCC1.Cl>O.CC#N.O>[CH2:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:35])[CH2:15][NH:16][C:17]([C:19]2[N:20]=[C:21]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[S:22][C:23]=2[NH:24][CH2:25][CH2:26][C:27]([OH:38])=[O:28])=[O:18])[CH2:12][CH2:13]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2724126TempoHCID 21865429Bis(acetoxy)iodobenzeneHCID 49764563HCID 49764563, compound

Product 1

HCID 49763447HCID 49763447, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

To a suspension of Example 27 (25 mg) in H2O/CH3CN (0.2 mL, 1:1) was added at 0° C. diacetoxyiodobenzene (35 mg) and 2,2,6,6-tetramethylpiperidine-1-oxyl (3 mg), and the reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was diluted with H2O, acidified with aq. HCl (1M, 0.5 mL) and extracted with EtOAc (3×5 mL) The combined organic layers were dried over Na2SO4 and concentrated to dryness. Purification by CC (CH2Cl2/MeOH 97:3) gave 8 mg of the desired product.

Workup

  1. extractionextracted with EtOAc (3×5 mL) The combined organic layers
  2. dry with materialwere dried over Na2SO4
  3. concentrationconcentrated to dryness
  4. customPurification by CC (CH2Cl2/MeOH 97:3)

Sources & evidence

ORD record
ord-f77f2d5918cd4eeba1c4ff7499170654
Source dataset
uspto-grants-2014_03
Patent number
US08664203B2

Reaction notes

Loading…