(3R-trans)-[(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)phenylamino]acetic acid, ethyl ester → (3R-trans)-4-[N-(3-Furanylmethyl)phenylamino]-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 356668Notes

Reaction equation

HRID 356668 reaction equation
[CH3:1][C:2]1([CH3:15])[C@@H:7]2[O:8][C@@H:6]2[C:5]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:4]=2[O:3]1.C(C1C=C[C:21]2[O:26][C:25](C)(C)[C@H:24](O)[C@@H:23]([N:30](CC(OCC)=O)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:22]=2C=1)#N>CO>[O:26]1[CH:21]=[CH:22][C:24]([CH2:23][N:30]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C@H:6]2[C:5]3[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:4]=3[O:3][C:2]([CH3:15])([CH3:1])[C@@H:7]2[OH:8])=[CH:25]1

Participants

4

Reactant 2

HCID 10738551(3R-trans)-[(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)phenylamino]acetic acid, ethyl esterHCID 10987295(1aR,7bR)-2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrile

Product 1

HCID 67800715(3R-trans)-4-[N-(3-Furanylmethyl)phenylamino]-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared from (1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno-[c][1]benzopyran-6-carbonitrile (the title A compound of Example 3) and the title A compound by the same procedure as described for the title compound of Example 1. The product was obtained as a colorless solid (0.85 g, 57%), mp 63°-67° C. [α]D =+65.2° (c=0.71 MeOH). Analysis calculated for C23H22N2O3 ·0.25H2O: C, 72.90; H, 5.98; N, 7.39. Found: C, 72.94; H, 5.95; N, 7.35.

Sources & evidence

ORD record
ord-2d9c3ec0b63841a78e38397438d2e403
Source dataset
uspto-grants-1998_11
Patent number
US05837702

Reaction notes

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