Hydrochloric Acid → HCID 59605380, compound

HRID 1946091Notes

Reaction equation

HRID 1946091 reaction equation
[CH3:1][CH:2]([CH3:40])[CH:3]([N:9]1[CH2:12][CH:11]([CH2:13][C:14]2[N:15]([CH3:39])[C:16]3[C:21]([N:22]=2)=[C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:19]=[C:18]([N:29]2[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[N:31]=[C:30]2[CH3:38])[N:17]=3)[CH2:10]1)[C:4]([O:6]CC)=[O:5].C(O)C.[OH-].[Li+].Cl>O>[CH3:1][CH:2]([CH3:40])[CH:3]([N:9]1[CH2:10][CH:11]([CH2:13][C:14]2[N:15]([CH3:39])[C:16]3[C:21]([N:22]=2)=[C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:19]=[C:18]([N:29]2[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[N:31]=[C:30]2[CH3:38])[N:17]=3)[CH2:12]1)[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3939Lithium HydroxideHCID 59605889HCID 59605889, compound

Product 1

HCID 59605380HCID 59605380, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 3-methyl-2-(3-((9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methyl)azetidin-1-yl)butanoate (0.180 g, 0.329 mmol) in ethanol (1.0 mL, 17 mmol) was added 1.0 M of lithium hydroxide in water (2.0 mL). The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was neutralized with 1M HCl and concentrated. The residue was re-dissolved in MeOH and loaded onto a SCX-2 column. The column was first washed with MeOH. The product was then eluted with 2M NH3 in MeOH and concentrated. LCMS m/z: 519.3 (MH+)

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was re-dissolved in MeOH
  3. washThe column was first washed with MeOH
  4. washThe product was then eluted with 2M NH3 in MeOH
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f67c090a1a94a239d9b11e8a669debe
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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