Water → HCID 59026202, compound

HRID 639072Notes

Reaction equation

HRID 639072 reaction equation
C1(COC(=O)[NH:10][CH2:11][C@@H:12]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([O:29][CH3:30])[N:27]=4)[N:22]=[CH:21][C:20]=3[Cl:31])[CH2:13]2)C=CC=CC=1.[OH-].[K+].O>CO>[Cl:31][C:20]1[CH:21]=[N:22][C:23]2[C:28]([C:19]=1[CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][C@@H:12]([CH2:11][NH2:10])[CH2:13]1)=[N:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 59026200phenylmethyl[((3S)-1-{2-[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate

Product 1

HCID 59026202HCID 59026202, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of phenylmethyl[((3S)-1-{2-[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate (1.0 g, 2.2 mmol) in MeOH (30 mL) was treated with 40% KOH (15 mL, 107 mmol) and heated at 100° C. for 3 h. The MeOH was stripped off at reduced pressure and the residue was treated with water. The product was extracted into CHCl3 and the combined organic phases were dried (K2CO3) and filtered. Purification of silica gel provided the product as a light brown oil (0.36 g, 51%): LC/MS (ES) m/e 321 (M+H)+.

Workup

  1. extractionThe product was extracted into CHCl3
  2. dry with materialthe combined organic phases were dried (K2CO3)
  3. filtrationfiltered
  4. customPurification of silica gel

Sources & evidence

ORD record
ord-9a4ea01987de43a38e469dd519693ca5
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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