3-Mercaptopropanol → (2R,3R)-2-(2,4-Difluorophenyl)-3-[(3-hydroxypropyl)thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanol

HRID 2395687Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([CH2:13][N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[C@@H:11]([CH3:12])[O:10]1.[SH:19][CH2:20][CH2:21][CH2:22][OH:23]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:10])([C@H:11]([S:19][CH2:20][CH2:21][CH2:22][OH:23])[CH3:12])[CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1

Participants

Reactant 2

HCID 882113-Mercaptopropanol

HCID 107058781-(((2R,3R)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole

Product 1

HCID 15234257(2R*,3R*)-2-(2,4-Difluorophenyl)-3-[(3-hydroxypropyl)thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanolYield 61.5%

Procedure

Following a procedure similar to that described in Example 1, but using 50 mg of (2R*,3R*)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane [prepared as described in Chem. Pharm. Bull., 38, 2476 (1990), Oida et al.] and 54 mg of 3-mercaptopropanol, 42 mg of the title compound, melting at 119°-120° C. (after recrystallization from a mixture of ethyl acetate and benzene), were obtained.

Sources & evidence

ORD record: ord-f35a4b521f0e4f9c9312cf930327e5b1
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05489606

Reaction notes

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