Methanol → HCID 24886519, compound

HRID 722268Notes

Reaction equation

HRID 722268 reaction equation
C(=O)([O-])[O-].[K+].[K+].CO.C(O[CH2:13][C:14]([N:16]([C@@H:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][C@H:22]1[NH:30][C:31]([C:33]1[NH:34][C:35]2[C:40]([CH:41]=1)=[CH:39][C:38]([Cl:42])=[CH:37][CH:36]=2)=[O:32])[CH2:17][C:18]([OH:20])=[O:19])=[O:15])(=O)C>C1COCC1>[Cl:42][C:38]1[CH:39]=[C:40]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33]([C:31]([NH:30][C@@H:22]1[CH2:23][C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:21]1[N:16]1[C:14](=[O:15])[CH2:13][O:19][C:18](=[O:20])[CH2:17]1)=[O:32])=[CH:41]2

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 24886518HCID 24886518, compound

Product 1

HCID 24886519HCID 24886519, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium carbonate (20 mg) and MeOH (1 mL) were added to a solution of N-{(1R,2R)-1-[N-(2-acetoxyacetyl)-N-(carboxymethyl)amino]-2,3-dihydro-1H-inden-2-yl}-5-chloroindole-2-carboxamide (Example 35, 184 mg, 0.38 mmol) in THF (5 mL) and the reaction was stirred at ambient temperature for 24 h. The volatiles were removed by evaporation under reduced pressure, the residue dissolved in water and acidified to pH 2.0 and then extracted into EtOAc (3×10 mL). The volatiles were removed by evaporation under reduced pressure and the residue purified by column chromatography (EtOAc:isohexane 1:4) to afford the title compound (50 mg, 31%) as a white solid.

Workup

  1. customThe volatiles were removed by evaporation under reduced pressure
  2. dissolutionthe residue dissolved in water
  3. extractionextracted into EtOAc (3×10 mL)
  4. customThe volatiles were removed by evaporation under reduced pressure
  5. customthe residue purified by column chromatography (EtOAc:isohexane 1:4)

Sources & evidence

ORD record
ord-1e01c7e256a34841ab9959e1aa2c9690
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

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