Lithium Hydroxide → Isoquinoline-1-carboxylic acid

HRID 891201Notes

Reaction equation

HRID 891201 reaction equation
COC(=O)CN1CC(CNCC2C=CC=CC=2)=CCC(N[C:22]([C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26][N:25]=2)=[O:23])C1=O.[Li+].[OH-:37]>C1COCC1.O>[C:24]1([C:22]([OH:23])=[O:37])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][N:25]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 23598690HCID 23598690, compound

Product 1

HCID 68092Isoquinoline-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution containing {6-(benzylamino-methyl)-3-[(isoquinoline-1-carbonyl)-amino]-2-oxo-2,3,4,7-tetrahydro-azepin-1-yl}-acetic acid methyl ester, 24, (82 mg, 0.14 mmol) in THF/H2O (4 mL of 3:1) is treated with excess LiOH and stirred for 2.5 hours at room temperature. The solution is acidified to pH 7 and concentrated in vacuo. The residue is purified by HPLC to afford the desired product which is used directly for the next step.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-66e63e325a87452e8f4c03954eb8ea33
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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