Lithium hydroxide, monohydrate → HCID 68710732, compound

HRID 1927807Notes

Reaction equation

HRID 1927807 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[NH:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)=[O:10])C1C=CC=CC=1.O.[OH-].[Li+]>C1COCC1.O.C(OCC)(=O)C>[CH3:25][O:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[C:17]([NH:16][N:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[C:9]([OH:10])=[O:8])=[O:26]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68709175HCID 68709175, compound

Product 1

HCID 68710732HCID 68710732, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

(2S)-1-(3-Methoxybenzoylamino)pyrrolidine-2-carboxylic acid benzyl ester (654 mg, 1.93 mmol) was dissolved in THF/H2O (9:1, 10 ml). Lithium hydroxide monohydrate (243 mg, 5.79 mmol) was added. After 18 h at room temperature the reaction mixture was diluted with ethyl acetate (50 ml). This solution was washed with 1M KHSO4, water and brine, dried (Na2SO4) and evaporated in vacuo to give a colourless oil identified as the title compound (470 mg, 1.89 mmol, 98%).

Workup

  1. washThis solution was washed with 1M KHSO4, water and brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customto give a colourless oil

Sources & evidence

ORD record
ord-dcd04cef555844778ded69f22d02a365
Source dataset
uspto-grants-2012_05
Patent number
US08183280B2

Reaction notes

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