5-Methyl-2-(trifluoromethyl)-3-furanmethanol → 3-[5-Chloro-2-(5-methyl-2-trifluoromethyl-furan-3-ylmethoxy)-phenoxy]-azetidine-1-carboxylic acid tert-butyl ester

HRID 237253Notes

Reaction equation

HRID 237253 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([F:10])([F:9])[F:8])=[C:4]([CH2:11][OH:12])[CH:3]=1.[C:13]([O:17][C:18]([N:20]1[CH2:23][CH:22]([O:24][C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=2O)[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>>[C:13]([O:17][C:18]([N:20]1[CH2:23][CH:22]([O:24][C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=2[O:12][CH2:11][C:4]2[CH:3]=[C:2]([CH3:1])[O:6][C:5]=2[C:7]([F:10])([F:8])[F:9])[CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

3

Reactant 2

HCID 27798975-Methyl-2-(trifluoromethyl)-3-furanmethanolHCID 673429093-(5-Chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 673484643-[5-Chloro-2-(5-methyl-2-trifluoromethyl-furan-3-ylmethoxy)-phenoxy]-azetidine-1-carboxylic acid tert-butyl ester

Procedure

Synthesized from the title compound of Step A and 3-(5-chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester using general procedure 7. MS (ESI): mass calcd. for C21H23ClF3NO5, 461.1; m/z found, 485.9 [M+Na]+. 1H NMR 6.91 (dd, J=8.6, 2.3 Hz, 1H), 6.84 (d, J=8.6 Hz, 1H), 6.55 (d, J=2.3 Hz, 1H), 6.22 (s, 1H), 5.07-5.00 (m, 2H), 4.90-4.81 (m, 1H), 4.30 (ddd, J=9.7, 6.5, 0.8 Hz, 2H), 4.06 (dd, J=9.8, 4.0 Hz, 2H), 2.34 (s, 3H), 1.45 (s, 9H).

Sources & evidence

ORD record
ord-2b8f0e302bb44ce79c0512a264b75a97
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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