Sodium Hydroxide → HCID 67080406, compound

HRID 510653Notes

Reaction equation

HRID 510653 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:39]=[CH:38][C:17]([C:18]([NH:20][C:21]3[CH:30]=[C:29]4[C:24]([CH2:25][CH2:26][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:28]4)=[CH:23][CH:22]=3)=[O:19])=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:40]([O:42]C)=[O:41])#[N:2].[OH-].[Na+]>CO.O1CCCC1>[C:34]([O:33][C:31]([N:27]1[CH2:26][CH2:25][C:24]2[C:29](=[CH:30][C:21]([NH:20][C:18]([C:17]3[CH:38]=[CH:39][C:14]([O:13][C:12]4[CH:11]=[C:10]5[C:5]([CH:6]([C:40]([OH:42])=[O:41])[CH2:7][CH2:8][O:9]5)=[CH:4][C:3]=4[C:1]#[N:2])=[CH:15][CH:16]=3)=[O:19])=[CH:22][CH:23]=2)[CH2:28]1)=[O:32])([CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67080920HCID 67080920, compound

Product 1

HCID 67080406HCID 67080406, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 7-(4-(6-cyano-4-(methoxycarbonyl)chroman-7-yloxy)benzamido)-3,4-dihydroisoquinoline-2(1H)-carboxylate (84 mg, 0.14 mmol) in a mixture of methanol (1 mL) and tetrahydrofuran (0.5 mL) was added 2M sodium hydroxide (0.36 mL, 0.72 mmol). The resulting solution was stirred at ambient temperature for 1 hour, then concentrated. The residue was partitioned between ethyl acetate (10 mL) and 1M hydrochloric acid (5 mL). The organic layer was dried over sodium sulfate and concentrated to afford 7-(4-(2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-7-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylic acid as an orange oil (40 mg, 49% yield).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate (10 mL) and 1M hydrochloric acid (5 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-223f617d21bc41679b7681c237511d6b
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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