Lithium Hydroxide → HCID 58015218, compound

HRID 2093404Notes

Reaction equation

HRID 2093404 reaction equation
[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C:9]1[N:14]=[CH:13][C:12]([C:15]2[N:23]=[C:22]3[C:18]([N:19]=[CH:20][N:21]3[CH2:24][C:25]([O-:27])=[O:26])=[C:17]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[N:16]=2)=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C:9]1[N:10]=[CH:11][C:12]([C:15]2[N:23]=[C:22]3[C:18]([N:19]=[CH:20][N:21]3[CH2:24][C:25]([OH:27])=[O:26])=[C:17]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[N:16]=2)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86637238HCID 86637238, compound

Product 1

HCID 58015218HCID 58015218, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Crude 2-(2-(2-(bis(tert-butoxycarbonyl)amino)pyrimidin-5-yl)-6-morpholino-9H-purin-9-yl)acetate (240 mg) was reacted with 3 eq of lithium hydroxide in 1:1 THF/water solution. After completion, the THF was concentrated in vacuo and the water solution was acidified to pH 2 using a concentrated HCl solution. The product precipitated as a fine white solid and was filtered to yield 2-(2-(2-(tert butoxycarbonylamino)pyrimidin-5-yl)-6-morpholino-9H-purin-9-yl)acetic acid (145 mg), of which 40 mg was subjected to General Procedure E and purified via reverse phase HPLC to give 19.5 mg 125 as a white solid. MS (Q1) 357.2 (M)+

Workup

  1. concentrationAfter completion, the THF was concentrated in vacuo
  2. customThe product precipitated as a fine white solid
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-34062591f39c4c5394971b9b3e17fba4
Source dataset
uspto-grants-2013_05
Patent number
US08445487B2

Reaction notes

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