Hydrochloric Acid → HCID 67367711, compound

HRID 1910973Notes

Reaction equation

HRID 1910973 reaction equation
[OH2:1].[OH-].[Li+].[F:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[O:16][C:15](=[O:17])[C:14]3=[CH:18][CH:19]=[C:20]([CH3:21])[N:13]3[CH2:12]2)=[CH:7][CH:6]=1.Cl>O.C1COCC1.CCOC(C)=O>[F:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:16])[CH2:12][N:13]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:14]2[C:15]([OH:1])=[O:17])=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67368771HCID 67368771, compound

Product 1

HCID 67367711HCID 67367711, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of lithium hydroxide hydrate (103 mg, 2.4 mmol) in water (1 mL) was added to a solution of 3-(4-fluorophenyl)-6-methyl-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazin-1-one (200 mg, 0.8 mmol) in THF (9 mL) at room temperature. The reaction was stirred at room temperature for 2 days. The reaction mixture was then diluted with EtOAc (20 mL) and acidified to approx. pH 2 with 1 M HCl (aq). The organic layer was separated and the aqueous layer extracted further with EtOAc (2×20 mL). The combined organic layers were washed with water, dried (MgSO4), filtered and concentrated in vacuo to give 1-[2-(4-fluorophenyl)-2-hydroxyethyl]-5-methyl-1H-pyrrole-2-carboxylic acid as an off-white solid (211 mg, 98%). 1H NMR (400 MHz, CD3OD): δ 2.07 (s, 3H), 4.31 (dd, 1H, J 13.7, 7.9 Hz), 4.42 (dd, 1H, J 13.7, 4.9 Hz), 4.99 (dd, 1H, J 7.7, 5.1 Hz), 5.85 (dd, 1H, J 3.9, 0.7 Hz), 6.92 (d, 1H, J 3.9 Hz), 6.97-7.06 (m, 2H), 7.34 (dd, 2H, J 8.5, 5.5 Hz).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted further with EtOAc (2×20 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f31c087a7b55474f831d2f8348580baf
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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