Methanol → HCID 68480779, compound

HRID 1874983Notes

Reaction equation

C([C:4]1[NH:8][C:7]([C:9]([O:11]C)=[O:10])=[C:6]([Cl:13])[CH:5]=1)(=O)C.CO.[Li+].[OH-].C1C[O:21][CH2:20][CH2:19]1>>[C:20]([C:5]1[C:6]([Cl:13])=[C:7]([C:9]([OH:11])=[O:10])[NH:8][CH:4]=1)(=[O:21])[CH3:19]

Participants

Reactant 4

HCID 887Methanol

HCID 3939Lithium Hydroxide

HCID 8028Tetrahydrofuran

HCID 68487863HCID 68487863, compound

Product 1

HCID 68480779HCID 68480779, compoundYield 67%

Conditions

Temperature: 60 °C

Procedure

Methyl 5-acetyl-3-chloro-1H-pyrrole-2-carboxylate (0.034 g, 0.169 mmol) was dissolved in THF (1 mL), methanol (1 mL) and 1N LiOH (1 mL). The reaction mixture was heated to 60° C. and stirred. The reaction mixture was evaporated and purification was accomplished by reverse-phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.033 g, 67%) as an impure product which was used with no further purification. LCMS: m/z 187.9 (M+1).

Workup

customThe reaction mixture was evaporated
custompurification

Sources & evidence

ORD record: ord-3f23d8f01932438eb6bc4cda94cdb490
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304419B2

Reaction notes

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