Sodium Hydroxide → HCID 86723434, compound

HRID 2201191Notes

Reaction equation

HRID 2201191 reaction equation
C(OC([N:11]([N:17]1[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:24]2[C:19]([N:20]([CH3:35])[C:21](=[O:34])[N:22]([CH3:33])[C:23]2=[O:32])=[CH:18]1)[CH2:12][CH2:13][C:14](O)=[O:15])=O)C1C=CC=CC=1.[OH-].[Na+]>O>[CH3:35][N:20]1[C:19]2=[C:18]3[C:14](=[O:15])[CH2:13][CH2:12][NH:11][N:17]3[C:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[C:24]2[C:23](=[O:32])[N:22]([CH3:33])[C:21]1=[O:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86723433HCID 86723433, compound

Product 1

HCID 86723434HCID 86723434, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-[Benzyloxycarbonyl-(1,3-dimethyl-2,4-dioxo-5-phenyl-1,2,3,4-tetrahydro-pyrrolo[3,4-d]pyrimidin-6-yl)-amino]-propionic acid (step 3) (1.09 g, 2.288 mmol) and Polyphosphoric acid (3 g, 2.288 mmol) were heated together at 100° C. (block temp) for 30 mins. The reaction mixture was cooled to RT and the residue dissolved in minimum volume of water. The mixture was basified by slow addition of 2M NaOH(aq), and extracted with chloroform (4×). The combined organic extracts were passed through a hydrophobic frit and evaporated under reduced pressure. Purification of the residue by chromatography on silica, eluting with MeOH/DCM afforded the title compound as a white solid.

Workup

  1. extractionextracted with chloroform (4×)
  2. customevaporated under reduced pressure
  3. customPurification of the residue by chromatography on silica
  4. washeluting with MeOH/DCM

Sources & evidence

ORD record
ord-169d2f2336e44e9bae587e85eda394ad
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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