Methanol → HCID 57461819, compound

HRID 1020385Notes

Reaction equation

HRID 1020385 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[O:9][C:10]([C:17]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([N:26]4[CH2:31][CH2:30][N:29]5[C:32](C(OCC)=O)=[N:33][N:34]=[C:28]5[CH2:27]4)=[N:24][CH:25]=3)=[O:18])=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=2)[CH2:3]1.C1COCC1.CO.[Li+].[OH-]>O>[N:34]1[N:33]=[CH:32][N:29]2[CH2:30][CH2:31][N:26]([C:23]3[N:24]=[CH:25][C:20]([NH:19][C:17]([C:10]4[O:9][C:8]([N:4]5[CH2:5][CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3]5)=[N:12][C:11]=4[C:13]([F:15])([F:16])[F:14])=[O:18])=[CH:21][CH:22]=3)[CH2:27][C:28]=12

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67390464HCID 67390464, compound

Product 1

HCID 57461819HCID 57461819, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 217 (64 mg) in 4:1:1 THF:MeOH:H2O (3 mL) was mixed with LiOH (15 mg), and stirred at r.t. overnight. The mixture was concentrated and purified by prep Gilson HPLC to give the decarboxylation product 218 (25 mg as a pale solid). 1H NMR (500 MHz, DMSO-d6) δ 10.08 (s, 1H), 8.49 (s, 1H), 8.42 (d, 1H, J=2.5 Hz), 7.89 (m, 1H), 7.11 (d, 1H, J=9.1), 4.86 (s, 2H), 4.10 (m, 6H), 3.05 (m, 1H), 2.75 (t, 1H, J=11.7 Hz), 1.77 (m, 2H), 1.67 (m, 1H), 1.53 (m, 1H), 1.15 (m, 1H), 0.94 (d, 3H, J=6.6 Hz). MS (M+1): 477.3

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by prep Gilson HPLC

Sources & evidence

ORD record
ord-3aee16dfbf9442769149b424324b9943
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

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