Isopropanol → HCID 89582603, compound

HRID 2276806Notes

Reaction equation

HRID 2276806 reaction equation
O[C@@H](C1C=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[N:8]=[C:7]([C:25](N)=[O:26])N=1)CO.FC1C=CC(OC2C=CC(C3[N:45]=[C:44]([C:46]([O:48]C)=[O:47])[CH:43]=C(C=C)N=3)=CC=2)=CC=1.[CH:54]([OH:57])(C)C>>[OH:26][C@@H:25]([C:7]1[N:8]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)=[CH:15][CH:16]=2)[N:45]=[C:44]([C:46]([OH:48])=[O:47])[CH:43]=1)[CH2:54][OH:57]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 71572205HCID 71572205, compoundHCID 89580281HCID 89580281, compound

Product 1

HCID 89582603HCID 89582603, compoundYield 80%

Procedure

(S)-6-(1,2-dihydroxyethyl)-2-(4-(4-fluorophenoxy)phenyl)pyrimidine-4-carboxylic acid (25) was prepared in a similar fashion to compound 20 (Scheme 3) using AD mix-α (1.51 g) and compound 24 (360 mg, 1.03 mmol) in aqueous isopropyl alcohol (i-PrOH:H2O=1:1). (304 mg, 80% yield); LC/MS: m/z=371[M+H]+.

Sources & evidence

ORD record
ord-f002125da5ca431587850b34489c6e1e
Source dataset
uspto-grants-2015_09
Patent number
US09133131B2

Reaction notes

Loading…