Ethyl Acetate → HCID 58392480, compound

HRID 561622Notes

Reaction equation

[C-:1]#[N:2].[K+].CS(O[CH2:9][CH2:10][C:11]([C:25]1[CH:34]=[CH:33][C:28]2[O:29][CH2:30][CH2:31][O:32][C:27]=2[CH:26]=1)([C:13]1[C:21]2[C:16](=[C:17]([CH2:22][S:23][CH3:24])[CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[CH3:12])(=O)=O.C(OCC)(=O)C>CS(C)=O>[O:29]1[C:28]2[CH:33]=[CH:34][C:25]([C:11]([C:13]3[C:21]4[C:16](=[C:17]([CH2:22][S:23][CH3:24])[CH:18]=[CH:19][CH:20]=4)[NH:15][CH:14]=3)([CH3:12])[CH2:10][CH2:9][C:1]#[N:2])=[CH:26][C:27]=2[O:32][CH2:31][CH2:30]1

Participants

Conditions

Temperature: 80 °C

Procedure

150 mg (2.30 mmol) of potassium cyanide were added to 530 mg (1.15 mmol) of the compound from Example 117A in 10 ml of DMSO. The mixture was stirred at 80° C. for 16 h, ethyl acetate was added to the reaction solution, and the mixture was washed twice with water and once with saturated aqueous sodium chloride solution. The combined organic phases were freed of solvent, and the crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 328 mg (73% of theory) of the target compound were obtained.

Workup

washthe mixture was washed twice with water and once with saturated aqueous sodium chloride solution
customthe crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)
custom328 mg (73% of theory) of the target compound were obtained

Sources & evidence

ORD record: ord-8723521c57ea4bbb85256cc1e4c0b199
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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