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

HRID 356675Notes

Reaction equation

HRID 356675 reaction equation
CC1(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]C)=O)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:22]=2[CH:43]=1)#[N:17]>>[OH:29][C@@H:24]1[C@@H:23]([N:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:37][CH2:38][O:40][CH3:41])[C:22]2[CH:43]=[C:18]([C:16]#[N:17])[CH:19]=[CH:20][C:21]=2[O:26][C:25]1([CH3:28])[CH3:27]

Participants

3

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 11792312(3R-trans)-3,4-Dihydro-3-hydroxy-4-[N-(2-methoxyethyl)-phenyl-amino]-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

Procedure

The title compound was prepared from the title A compound and (1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno-[c][1]benzopyran-6-carbonitrile (the title A compound of Example 3) by the procedure described for the title compound of Example 1. The oily residue was purified by flash chromatography on silica gel (ethyl acetate:hexanes/1:6), to give a colorless powder (410 mg, 77%), mp 119°-124° C. [α]D =+54.40 (c=0.43, MeOH). Analysis calculated for C21 H24N2O3 : C, 71.57; H, 6.86; N, 7.95. Found: C, 71.53; H, 6.94; N, 7.73.

Workup

  1. customThe oily residue was purified by flash chromatography on silica gel (ethyl acetate:hexanes/1:6)

Sources & evidence

ORD record
ord-31804e85199a4f17b0f07d79119dab2c
Source dataset
uspto-grants-1998_11
Patent number
US05837702

Reaction notes

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