Hydrochloric Acid → HCID 21098990, compound

HRID 1351750Notes

Reaction equation

HRID 1351750 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[C:9]([CH3:15])=[C:8]2[C:4]=1[C:5]1[CH2:19][CH2:18][O:17][C:16]([CH2:23][C:24]([O:26]CC)=[O:25])([CH2:20][CH2:21][CH3:22])[C:6]=1[NH:7]2)#[N:2].[OH-].[Na+].Cl>CCO>[C:24]([CH2:23][C:16]1([CH2:20][CH2:21][CH3:22])[C:6]2[NH:7][C:8]3[C:4]([C:5]=2[CH2:19][CH2:18][O:17]1)=[C:3]([C:1]#[N:2])[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[C:9]=3[CH3:15])([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21099228HCID 21099228, compound

Product 1

HCID 21098990HCID 21098990, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-Cyano-1-ethoxycarbonylmethyl-8-methyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indole-7-carboxylic acid (27.9 mg, 0.073 mmol) in EtOH (2 mL) was added 10% NaOH (200 μL). The solution was stirred for 18 hours, acidified with 3% HCl, and extracted with EtOAc (2×). The organic layers were combined, washed with brine, dried (Na2SO4) and concentrated in vacuo to afford 25.6 mg (99%) of the title compound as an off-white solid. 1H NMR (d6-DMSO) δ 11.42 (br s,1 H), 7.93 (s, 1H), 3.97 (m, 2H), 3.00 (d, J=13.8 Hz, 1H), 2.88 (m, 2H), 2.81 (s, 3H), 2.76 (d, J=13.8 Hz, 1H), 2.04 (m, 2H), 1.30 (m,1H), 0.80 (m, 4H). ESI MS m/z 355 (M−H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-763a4921f94d4b3aa83e4ebadbc0d943
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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