Lithium hydroxide, monohydrate → HCID 20767946, compound

HRID 2081123Notes

Reaction equation

HRID 2081123 reaction equation
[C:1]([O:5][C:6]([NH:8][C@:9]1([C:15]([O:17]CC)=[O:16])[CH2:11][C@H:10]1[CH:12]1[CH2:14][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.CO.O.O[Li].O>O>[C:1]([O:5][C:6]([NH:8][C@:9]1([C:15]([OH:17])=[O:16])[CH2:11][C@H:10]1[CH:12]1[CH2:14][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21892291Methanol tetrahydrofuran waterHCID 59990838(1R,2S)-ethyl 1-(tert-butoxycarbonylamino)-2-cyclopropylcyclopropanecarboxylate

Product 1

HCID 20767946HCID 20767946, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(1R,2S)-ethyl 1-(tert-butoxycarbonylamino)-2-cyclopropylcyclopropanecarboxylate (0.578 g, 2.15 mmol), was dissolved in 10 mL mixed solvent of THF:MeOH:water (2:2:1 v/v), followed by addition of LiOH—H2O (0.270 g, 6.44 mmol) in one portion at rt. Stirred it at rt over 2 days. After removal of most solvent, the white solid reaction residue was taken up in water (30 mL) and washed with ether (30 mL). The aqueous layer was then acidified with 1N HCl until pH reached 2. It was then extracted with EtOAc (2×50 mL), and the combined organic extract was washed with brine and dried over Na2SO4, giving the acid, (1R,2S)-1-(tert-butoxycarbonylamino)-2-cyclopropylcyclopropane carboxylic acid, as a white fluffy solid (0.48 g, 93%).

Workup

  1. customAfter removal of most solvent
  2. customthe white solid reaction residue
  3. washwashed with ether (30 mL)
  4. extractionIt was then extracted with EtOAc (2×50 mL)
  5. extractionthe combined organic extract
  6. washwas washed with brine
  7. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-73ad1e5c96ac472d90a57302fcf77ded
Source dataset
uspto-grants-2011_04
Patent number
US07932277B2

Reaction notes

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