(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-(2-Furanylmethyl)phenylamino]-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 356670Notes

Reaction equation

HRID 356670 reaction equation
[CH3:1]C1(C)[C@@H]2O[C@@H]2C2C=C(C#N)C=CC=2O1.[C:16]([C:18]1[CH:19]=[CH:20][C:21]2[O:26][C:25]([CH3:28])([CH3:27])[C@H:24]([OH:29])[C@@H:23]([N:30]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=O)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:22]=2[CH:43]=1)#[N:17]>CO>[O:40]1[CH:41]=[CH:42][CH:1]=[C:38]1[CH2:37][N:30]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C@H:23]1[C:22]2[CH:43]=[C:18]([C:16]#[N:17])[CH:19]=[CH:20][C:21]=2[O:26][C:25]([CH3:28])([CH3:27])[C@@H:24]1[OH:29]

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 10667126(3R-trans)-4-[N-(2-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 (1.07 g, 72%), mp 134°-135° C. [α]D =+92.20° (c=0.78, MeOH). Analysis calculated for C23H22N2O3 · 0.02 H2O: C, 73.70; H, 5.93; N, 7.47. Found: C, 73.65; H, 5.63; N, 7.52.

Sources & evidence

ORD record
ord-b0325644236041989bd607add950cf4d
Source dataset
uspto-grants-1998_11
Patent number
US05837702

Reaction notes

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