Formic Acid → HCID 89648546, compound

HRID 1773938Notes

Reaction equation

HRID 1773938 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[C:14]([C:22]3[C:27]([O:28][CH3:29])=[CH:26][C:25]([CH2:30][C:31]([O:33]CC)=[O:32])=[CH:24][C:23]=3[O:36][CH3:37])[CH:15]=[CH:16][C:17]=2[F:21])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)=O>CN(C=O)C.[OH-].[Na+]>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[C:14]([C:22]3[C:23]([O:36][CH3:37])=[CH:24][C:25]([CH2:30][C:31]([OH:33])=[O:32])=[CH:26][C:27]=3[O:28][CH3:29])[CH:15]=[CH:16][C:17]=2[F:21])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 118353196HCID 118353196, compound

Product 1

HCID 89648546HCID 89648546, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 8-(4-ethoxycarbonylmethyl-2,6-dimethoxy-phenyl)-5-fluoro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (9.5 mg, 0.02 mmol, 1 eq.) in DMF (0.1 mL), 2M aq. NaOH soln. (68 μL) was added. The solution was stirred at r.t. for 18 hours. Formic acid was added (0.1 mL). The resulting acidic solution was purified by prep. HPLC (column: Waters XBridge, 19×30 mm, 10 um, UV/MS, acidic conditions) and evaporated to give the desired acid as a white solid.

Workup

  1. addition(68 μL) was added
  2. customThe resulting acidic solution was purified by prep
  3. customHPLC (column: Waters XBridge, 19×30 mm, 10 um, UV/MS, acidic conditions) and evaporated

Sources & evidence

ORD record
ord-26daf06dc39b48938ceb5735f613026e
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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