Tetrahydrofuran → HCID 22870807, compound

HRID 976464Notes

Reaction equation

HRID 976464 reaction equation
[NH2:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:3]([NH:5][C@@H:6]1[C:11]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:10]=2[O:9][C:8]([CH3:19])([CH3:18])[C@H:7]1[OH:20])=[O:4].[O:27]1CC[CH2:29][CH2:28]1>CO>[C:16]([C:13]1[CH:14]=[CH:15][C:10]2[O:9][C:8]([CH3:19])([CH3:18])[C@@H:7]([OH:20])[C@H:6]([NH:5][C:3](=[O:4])[CH:2]([NH:1][C:28](=[O:27])[CH3:29])[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:11]=2[CH:12]=1)#[N:17]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 57318853HCID 57318853, compound

Product 1

HCID 22870807HCID 22870807, compound

Reagents, catalysts & solvents 1

HCID 887MethanolCatalyst

Procedure

To a solution containing (3S-trans)-α-amino-N-(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)benzeneacetamide (340 mg, 0.97 mmol; isomer A of the title compound of Example 2) in tetrahydrofuran (10 mL, a few drops of methanol were added to obtain a clear solution) at room temperature was slowly added excess acetyl chloride while maintaining the reaction at pH ~8.5 by simultaneous addition of 7% sodium carbonate solution. After the completion of the reaction, it was diluted with ethyl acetate and washed with water and brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated to provide a colorless solid (320 mg, 84.2%) which was recrystallized from hot 2-propanol to give (3S-trans)-N-[2-[(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl )amino]-2-oxo-1-phenylethyl]acetamide, mp 234°-236° C. Analysis calculated for C22H23N3O4.0.2H2O: C, 66.55; H, 5.94; N, 10.58. Found: C, 66.71; H, 5.58; N, 10.56. [α]D =-91.2° (c =0.5, MeOH).

Sources & evidence

ORD record
ord-5b72831568804852866d76e07f3173fb
Source dataset
uspto-grants-1997_03
Patent number
US05612370

Reaction notes

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