Lithium Hydroxide → HCID 66909826, compound

HRID 2093400Notes

Reaction equation

HRID 2093400 reaction equation
BrCCC(OC)=O.[C:8]([O:12][C:13]([N:15](C(OC(C)(C)C)=O)[C:16]1[N:21]=[CH:20][C:19]([C:22]2[N:30]=[C:29]3[C:25]([N:26]=[CH:27][N:28]3[CH2:31][CH2:32][C:33]([O:35]C)=[O:34])=[C:24]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)[N:23]=2)=[CH:18][N:17]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[OH-].[Li+]>C1COCC1.O>[C:8]([O:12][C:13]([NH:15][C:16]1[N:17]=[CH:18][C:19]([C:22]2[N:30]=[C:29]3[C:25]([N:26]=[CH:27][N:28]3[CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[C:24]([N:37]3[CH2:38][CH2:39][O:40][CH2:41][CH2:42]3)[N:23]=2)=[CH:20][N:21]=1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 76934Methyl 3-bromopropanoateHCID 66909837HCID 66909837, compound

Product 1

HCID 66909826HCID 66909826, compoundYield 103%

Reagents, catalysts & solvents 1

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

Procedure

2-(2-(2-(Bis(tert-butoxycarbonyl)amino)pyrimidin-5-yl)-6-morpholino-9H-purin-2-yl (400 mg) was reacted with methyl 3-bromopropionate via General Procedure C. The product, 468 mg of crude methyl 3-(2-(2-(bis(tert-butoxycarbonyl)amino)pyrimidin-5-yl)-6-morpholino-9H-purin-9-yl)propanoate, was reacted with 3 eq of lithium hydroxide in 1:1 THF/Water solution. After completion, the THF was removed under vacuum and the water solution was acidified to pH 2 using a concentrated HCl solution. The product precipitated as a white solid and was filtered to yield 388 mg 3-(2-(2-(tert butoxycarbonylamino)pyrimidin-5-yl)-6-morpholino-9H-purin-9-yl)propanoic acid of which 88 mg was subjected to Boc deprotection via General Procedure E to give 15.5 mg 114 as white solid following reverse phase purification. MS (Q1) 371.2 (M)+

Workup

  1. customAfter completion, the THF was removed under vacuum
  2. customThe product precipitated as a white solid
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-56158459a3754ee794f0cf99f6bf3d13
Source dataset
uspto-grants-2013_05
Patent number
US08445487B2

Reaction notes

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