Tetrahydrofuran → HCID 22135205, compound

HRID 491009Notes

Reaction equation

HRID 491009 reaction equation
[CH3:1][CH:2]([CH3:17])[CH2:3][CH2:4][NH:5][C:6]([C:8]1([C:13]([O:15]C)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].O.[OH-].[Li+].[CH2:21]1COCC1>O.Cl>[CH3:21][CH:9]1[CH2:10][CH2:11][CH2:12][C:8]1([C:6](=[O:7])[NH:5][CH2:4][CH2:3][CH:2]([CH3:17])[CH3:1])[C:13]([OH:15])=[O:14]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 22135199HCID 22135199, compound

Product 1

HCID 22135205HCID 22135205, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 1-[N-(3-methylbutyl)carbamoyl]cyclopentanecarboxylate (820 mg, 3.4 mmol) in 25 mL of THF cooled to 0° C. was added dropwise a solution of lithium hydroxide monohydrate (260 mg, 6.12 mmol) in 5.0 mL of water. The reaction mixture was stirred at rt for 16 h. THF was removed under reduced pressure to give a yellow oil which was diluted with 10 mL of 1N HCl. The aqueous phase was extracted with CH2Cl2 (8×15 mL), and the extracts were combined, dried over Na2SO4, and concentrated to afford 700 mg (90%) of methyl 1-[N-(3-methylbutyl)carbamoyl]-cyclopentanecarboxylic acid as a white solid. MS [M+H]+ 228.

Workup

  1. customTHF was removed under reduced pressure
  2. customto give a yellow oil which
  3. extractionThe aqueous phase was extracted with CH2Cl2 (8×15 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-654547e92aad4c70a0ee1fb27740942a
Source dataset
uspto-grants-2009_05
Patent number
US07528249B2

Reaction notes

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