Lithium hydroxide, monohydrate → HCID 67459086, compound

HRID 625063Notes

Reaction equation

HRID 625063 reaction equation
[OH:1][Li].O.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:17][C:14]3([CH2:16][CH2:15]3)[N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:12]2=[O:25])=[CH:7][CH:6]=1>O.CO.C1COCC1>[C:21]([O:20][C:18]([NH:13][C:14]1([CH2:17][CH:11]([C:8]2[CH:9]=[CH:10][C:5]([Cl:4])=[CH:6][CH:7]=2)[C:12]([OH:25])=[O:1])[CH2:16][CH2:15]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67459938HCID 67459938, compound

Product 1

HCID 67459086HCID 67459086, compoundYield 86.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH hydrate (0.24 g, 5.7 mmol) in water (2 mL) was added to a stirred solution of tert-butyl 6-(4-chlorophenyl)-5-oxo-4-azaspiro[2.4]heptane-4-carboxylate (0.46 g, 1.4 mmol) in MeOH (2 mL) and THF (2 mL). The reaction was stirred at room temperature overnight. The solvents were evaporated in vacuo. The residue was taken up in water and extracted with ether (2×). The aqueous phase was acidified by 2N HCl and extracted with EtOAc. The combined organic phases were washed with brine, dried and concentrated to give 3-(1-(tert-butoxycarbonylamino)cyclopropyl)-2-(4-chlorophenyl)propanoic acid (0.41 g, 84%) as a white solid. LCMS (APCI+) [M-Boc+H]+ 240.0; Rf: 2.38 min.

Workup

  1. customThe solvents were evaporated in vacuo
  2. extractionextracted with ether (2×)
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-22838617c38647f7973e351f788f3147
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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