Hydrochloric Acid → HCID 22676794, compound

HRID 1006283Notes

Reaction equation

HRID 1006283 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[C:15]([C:29]([O:31]CC)=[O:30])=[C:14]2[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH:42]2[CH2:44][CH2:43]2)=[CH:36][CH:35]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>CO.O>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[C:15]([C:29]([OH:31])=[O:30])=[C:14]2[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH:42]2[CH2:43][CH2:44]2)=[CH:36][CH:35]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22676735HCID 22676735, compound

Product 1

HCID 22676794HCID 22676794, compoundYield 40.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1 M Aqueous sodium hydroxide (1 mL) was added to a stirred solution of ethyl 5-(benzyloxy)-3-[4-(cyclopropylmethoxy)phenyl]-1-(3-methoxybenzyl)-1H-indole-2-carboxylate (Example 61, 100 mg, 0.178 mmol) in methanol (1 mL). The reaction was warmed (50° C.) and stirring was continued for 18 h. After cooling the reaction was diluted with water (20 mL) and then the solution was adjusted to pH=2 using 1 M hydrochloric acid. The product was extracted with ethyl acetate (3×20 mL) and then the combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Flash chromatography of the residue over silica gel using 50% ethyl acetate/hexane gave 38.4 mg (40%) of the desired product as a pure white solid (mp=185-187° C.). The product had: 1H NMR (300 MHz, CDCl3) δ 7.25-7.48 (m, 8 H), 6.89-7.17 (m, 3 H), 6.65-6.78 (m, 2 H), 5.83 (s, 2 H), 5.05 (s, 2 H), 3.84 (d, 2 H), 3.68 (s, 3 H), 1.25-1.35 (m, 1 H), 0.57-0.67 (m, 2 H), 0.31-0.41 (m, 2 H); mass spectroscopy gave MH+=534.1 (calcd exact mass for C34H31NO5=533.22).

Workup

  1. temperatureAfter cooling the reaction
  2. extractionThe product was extracted with ethyl acetate (3×20 mL)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-476a483f7a3b4a6892cb5a20a7f00664
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

Loading…