Trifluoroacetic acid → HCID 131726451, compound

HRID 1352204Notes

Reaction equation

HRID 1352204 reaction equation
[CH3:1][CH:2]([CH3:32])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[CH:20]([N:24]3[CH2:27][CH:26]([C:28]([O:30]C)=[O:29])[CH2:25]3)[CH2:19][CH2:18]4)[N:11]=2)=[CH:6][CH:5]=1.[OH-].[Na+].[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>CO>[OH:39][C:37]([C:36]([F:41])([F:40])[F:35])=[O:38].[CH3:1][CH:2]([CH3:32])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[CH:20]([N:24]3[CH2:27][CH:26]([C:28]([OH:30])=[O:29])[CH2:25]3)[CH2:19][CH2:18]4)[N:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 21100039HCID 21100039, compound

Product 1

HCID 131726451HCID 131726451, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 1-(5-(5-(4-(2-methylpropyl)phenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)azetidine-3-carboxylate, Enantiomer 1 (from Step A, 0.10 g, 0.23 mmol) and sodium hydroxide (1N aqueous solution, 0.6 mL) were heated in methanol (1 mL) at 60° C. After 2 h, the reaction was cooled and acidified with trifluoroacetic acid. HPLC purification (HPLC B) gave the title compound as a white solid: 1H NMR (500 MHz, CD3OD) δ 8.19 (s, 1H), 8.13–8.15 (m, 3H), 7.74 (d, J=7.8 Hz, 1H), 7.44 (d, J=8.0 Hz, 2H), 5.06 (dd, J=2.5, 7.8 Hz, 1H), 4.52–4.60 (m, 2H), 4.41–4.48 (m, 2H), 3.71 (m, 1H), 3.27 (dt, J=8.15, 16.7 Hz, 1H), 3.13 (ddd, J=3.7, 9.2, 16.7 Hz, 1H), 2.56–2.66 (m, 3H), 2.22–2.30 (m, 1H), 1.92–2.00 (m, 1H), 0.96 (d, J=6.6 Hz, 6H); ESI-MS 418.1 (M+H).

Workup

  1. temperaturethe reaction was cooled
  2. customHPLC purification (HPLC B)

Sources & evidence

ORD record
ord-072fdcfe292f4b34a3f1e819202e7f65
Source dataset
uspto-grants-2007_05
Patent number
US07220734B2

Reaction notes

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