Lithium Hydroxide → HCID 58827104, compound

HRID 1877952Notes

Reaction equation

HRID 1877952 reaction equation
C[O:2][C:3]([C:5]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]#N)=[CH:15][C:14]=2[F:21])[N:9]2[CH:10]=[N:11][CH:12]=[C:8]2[CH2:7][CH2:6]1)=[O:4].[Li+].[OH-].C1C[O:27][CH2:26][CH2:25]1.CC[OH:31]>>[CH2:26]([O:27][C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:5]2([C:3]([OH:2])=[O:4])[N:9]3[CH:10]=[N:11][CH:12]=[C:8]3[CH2:7][CH2:6]2)=[C:14]([F:21])[CH:15]=1)=[O:31])[CH3:25]

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 21873804Tetrahydrofuran ethanolHCID 58827227HCID 58827227, compound

Product 1

HCID 58827104HCID 58827104, compound

Procedure

To a solution of 5-(4-cyano-2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole-5-carboxylic acid methyl ester (0.250 g, 0.877 mmol) in THF/EtOH (2:1, 21 mL) is added an aqueous solution of LiOH (0.88 mL, 2 M) is added. After 2.5 h the solution is concentrated and the resulting residue is purified by HPLC (2-23% MeCN/water containing 0.1% TFA). The title compound, 5-(4-ethoxycarbonyl-2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole-5-carboxylic acid, is isolated as a minor product. MS (ESI) m/z 319.0 (M+H).

Workup

  1. additionis added
  2. concentrationAfter 2.5 h the solution is concentrated
  3. customthe resulting residue is purified by HPLC (2-23% MeCN/water containing 0.1% TFA)

Sources & evidence

ORD record
ord-4e5da256f4ba40669eacd838d0083d64
Source dataset
uspto-grants-2012_11
Patent number
US08314097B2

Reaction notes

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