Citric Acid → HCID 178525550, compound

HRID 1713753Notes

Reaction equation

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

Participants

Conditions

Temperature: 35 °C

Procedure

A solution of lithium hydroxide (101 mg, 2.41 mmol) in H2O (1.5 mL) was added in one portion to a solution of methyl {trans-4-[4-({[5-(pyrimidin-4-ylamino)-1,3,4-oxadiazol-2-yl]-carbonyl}amino)phenyl]cyclohexyl}acetate (Example 416, 105 mg, 0.24 mmol) in a mixture of THF (1.8 mL) and MeOH (3 mL) and the reaction mixture was stirred at 35° C. for 2 h. Citric acid (50 mL) and EtOAc (50 mL) were added and the layers were separated and the aqueous layer was filtered to leave a solid. The solid was washed with water (10 mL) to give the title compound as a yellow brown solid (60 mg, 59%); 1H NMR δ 1.07-1.18 (2H, m), 1.41-1.51 (2H, m), 1.69-1.85 (5H, m), 2.14-2.16 (2H, d), 7.24 (2H, d), 7.71 (2H, d), 7.92 (1H, d), 8.69 (1H, d), 8.87 (1H, s), 11.00 (1H, s), 12.06 (2H, s); MS m/e MH+ 423.

Workup

customthe layers were separated
filtrationthe aqueous layer was filtered
customto leave a solid
washThe solid was washed with water (10 mL)

Sources & evidence

ORD record: ord-e37441fcca624beeae19735cd5e883fd
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795283B2

Reaction notes

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