1,1,1-Trifluoro-2-phenyl-3-butyn-2-ol → HCID 71621999, compound

HRID 926156Notes

Reaction equation

HRID 926156 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:30])[C:8]([CH:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22]CC)=[O:21])=[C:9]2[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[F:31][C:32]([F:44])([F:43])[C:33]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([OH:36])[C:34]#[CH:35]>>[C:26]([O:25][C@@H:19]([C:8]1[C:7]([CH3:30])=[CH:6][C:5]2[C:10](=[CH:11][C:2]([C:35]#[C:34][C:33]([OH:36])([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:32]([F:43])([F:44])[F:31])=[CH:3][CH:4]=2)[C:9]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:20]([OH:22])=[O:21])([CH3:29])([CH3:27])[CH3:28]

Participants

3

Reactant 2

HCID 27345751,1,1-Trifluoro-2-phenyl-3-butyn-2-olHCID 67126201Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

Product 1

HCID 71621999HCID 71621999, compound

Procedure

(2S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-7-(4,4,4-trifluoro-3-hydroxy-3-phenylbut-1-ynyl)naphthalen-2-yl)acetic acid was prepared by the method in Example 8 from ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate and 1,1,1-trifluoro-2-phenylbut-3-yn-2-ol. 1H-NMR: 400 MHz, (CD3OD) δ: 7.74 (m, 3H), 7.67 (s, 1H), 7.55 (m, 4H), 7.46 (m, 2H), 7.39 (m, 2H), 7.33 (m, 1H), 5.07 (s, 1H), 2.66 (s, 3H), 0.94 (s, 9H). LCMS-ESI+ (m/z): [M-OH]+ calcd for C31H32ClF3O3: 563.2. found: 563.1.

Sources & evidence

ORD record
ord-6570991e897b404fac937552cc73b780
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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