Sodium Hydroxide → HCID 58231461, compound

HRID 1434799Notes

Reaction equation

C([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:20])=[C:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH:10]=1)=[O:5])C.[OH-].[Na+]>O1CCOCC1>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][CH2:11][C:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[NH:7][C:8]=2[CH3:20])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-[2-(4-Chlorophenyl)-ethyl]-5-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (109) in dioxane, 10 equiv of NaOH aq (1.5 M) was added then the mixture was heated at 80° C. for 3 hours. When the reaction is judged complete, the solvent is removed under vacuum, H2O was added and an equal volume of Et2O was added. The organic layer was removed then the aqueous layer was made acidic with HCl (1M). If the product precipitates out at this point, it was filtered off, washed with H2O, and dried to obtain pure desired product. If the product didn't crash out when the aqueous layer is made acidic, Et2O was added, and the organic layer was removed (2×). The organic layer was dried with Na2SO4, filtered, and concentrated to obtain desired product. Purification: precipitation. Amount: 20.6 mg. 1H (MeOD 400 MHz): δ 7.2 (2H, dd), 7.08 (2H, dd), 6.59 (1H, s), 2.76 (2H, dd), 2.63 (2H, dd), 1.97 (3H, s) ppm. DEPT (CD3OD, 100 MHz): CH3: δ 10.8, CH2: □□ 28.9, 38.0, CH: 116.4, 129.1, 131.3 ppm. HPLC (20 min): 97.8%. LC/MS: 100%.

Workup

customthe solvent is removed under vacuum, H2O
additionwas added
additionan equal volume of Et2O was added
customThe organic layer was removed
customIf the product precipitates out at this point, it
filtrationwas filtered off
washwashed with H2O
customdried

Sources & evidence

ORD record: ord-2bca2e0de75e4f038934a34d38e922fb
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615572B2

Reaction notes

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