Hydrochloric Acid → HCID 59238302, compound

HRID 220188Notes

Reaction equation

HRID 220188 reaction equation
C[O:2][C:3](=[O:38])[CH:4]([C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21](=[O:37])[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:15][CH:14]=1)[CH2:5][CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH3:12].[Li+].[OH-].Cl>CO.O>[C:33]([O:32][C:30]([NH:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[NH:22][C:21](/[CH:20]=[CH:19]/[C:16]1[CH:15]=[CH:14][C:13]([CH:4]([CH2:5][CH2:6][CH:7]2[CH2:11][CH2:10][CH2:9][N:8]2[CH3:12])[C:3]([OH:38])=[O:2])=[CH:18][CH:17]=1)=[O:37])=[O:31])([CH3:36])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59238275HCID 59238275, compound

Product 1

HCID 59238302HCID 59238302, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of (E)-2-{4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-4-(1-methyl-pyrrolidin-2-yl)-butyric acid methyl ester (52.1 mg, 10 mmol) in MeOH/H2O (4:1) (2 mL), LiOH (24 mg, 100 mmol.) was added. After the solution was stirred at room temperature for 5 h, the solution was neutralized with 2N HCl to pH 5-6. The mixture was evaporated to dryness under reduced pressure, then EtOAc (10 mL) was added. The organic layer was washed with brine, dried with Na2SO4, filtered, and evaporated to obtain a yellow solid product without further purification. MS: calc'd 508 (MH+), exp 508 (MH+).

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. additionEtOAc (10 mL) was added
  3. washThe organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto obtain a yellow solid product
  8. customwithout further purification

Sources & evidence

ORD record
ord-96f7dd2b8dbc4594ada6f6dd6d33d1b3
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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