Sodium Hydroxide → HCID 57886968, compound

HRID 1819308Notes

Reaction equation

HRID 1819308 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]2[N:25]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:33])[C:24]3[C:23](=[O:34])[N:22]([CH3:35])[C:21](=[O:36])[N:20]([CH3:37])[C:19]=3[C:18]=2[C:38]([O:40]C)=[O:39])[CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[Cl-].[NH4+]>O1CCOCC1>[C:3]([O:7][C:8]([NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]2[N:25]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:33])[C:24]3[C:23](=[O:34])[N:22]([CH3:35])[C:21](=[O:36])[N:20]([CH3:37])[C:19]=3[C:18]=2[C:38]([OH:40])=[O:39])[CH2:12]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 57886978HCID 57886978, compound

Product 1

HCID 57886968HCID 57886968, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A 1M aqueous sodium hydroxide solution (10 ml) was added to a solution of methyl 6-{(3R)-3-[(tertbutoxycarbonyl)amino]piperidin-1-yl}-5-(2-chlorobenzyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidine-7-carboxylate (2.08 g) in 1,4-dioxane (10 ml), and the resulting mixture was stirred at 80° C. for 5 hours. After the reaction solution was cooled to 25° C., a saturated aqueous ammonium chloride solution was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then filtered and the filtrate was concentrated under reduced pressure to obtain the title compound (1.95 g) as a light-yellow amorphous substance.

Workup

  1. temperatureAfter the reaction solution was cooled to 25° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-44d9ce9921a4469985fb9ab7c7f190ac
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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