Sodium Hydroxide → HCID 67080406, compound

HRID 1021420Notes

Reaction equation

HRID 1021420 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-b2b356314a844e4f954f74af36ef5536
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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