Tetrahydrofuran → HCID 22870807, compound

HRID 976465Notes

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>>[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

Reactant 2

HCID 8028Tetrahydrofuran

HCID 57318853HCID 57318853, compound

Product 1

HCID 22870807HCID 22870807, compound

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 (600 mg, 1.7 mmol; isomer B of the title compound of Example 2)in tetrahydrofuran (7 mL) 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 gum (518 mg, 77.2%) which was stirred with ether 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 133°-145° C. (starts shrinking@124° C). Analysis calculated for C22H23N3O4.0.4H2O: C, 65.95; H, 5.99; N, 10.49. Found: C, 66.09; H, 5.92; N, 10.30. [α]D =+62.4° (c=0.5, MeOH).

Sources & evidence

ORD record: ord-d133db590efa4c90b60402ef9f91ba80
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05612370

Reaction notes

Loading…