Lithium Hydroxide → HCID 67078536, compound

HRID 480124Notes

Reaction equation

HRID 480124 reaction equation
C[O:2][C:3](=[O:39])[C@H:4]([NH:11][C:12]([C:14]12[CH2:21][C:18]([C:22]3[NH:30][C:29]4[C:28](=[O:31])[N:27]([CH2:32][CH2:33][CH3:34])[C:26](=[O:35])[N:25]([CH2:36][CH2:37][CH3:38])[C:24]=4[N:23]=3)([CH2:19][CH2:20]1)[CH2:17][CH2:16][CH2:15]2)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Li+].[OH-]>C1COCC1>[O:35]=[C:26]1[N:25]([CH2:36][CH2:37][CH3:38])[C:24]2[N:23]=[C:22]([C:18]34[CH2:21][C:14]([C:12]([NH:11][C@H:4]([C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:3]([OH:39])=[O:2])=[O:13])([CH2:20][CH2:19]3)[CH2:15][CH2:16][CH2:17]4)[NH:30][C:29]=2[C:28](=[O:31])[N:27]1[CH2:32][CH2:33][CH3:34]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67078535HCID 67078535, compound

Product 1

HCID 67078536HCID 67078536, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (1RS,2R,5SR)-{[5-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo-[3.2.1]octane-1-carbonyl]-amino}-phenyl-acetic acid methyl ester (0.022 mmol, 0.012 g) in THF (2 ml) was treated with 1N LiOH (0.22 ml) for 3d. The THF was removed on the rotovap, the aqueous residue acidified (pH 2) with 1N HCl and extracted with EtOAc. The combined organics were washed with H2O, brine and dried (MgSO4). Filtration and evaporation followed by reverse phase HPLC purification provide the desired product (0.0055 g, 48%) as a mixture of diastereomers. HPLC (10% to 90% MeCN (0.1% TFA)/H2O (0.1% TFA), YMC 120 A/S-5 ODS-AM column, 100 mm×4.6 mm, 1.5 ml/min: RT.=6.88 min.

Workup

  1. customThe THF was removed on the rotovap
  2. extractionextracted with EtOAc
  3. washThe combined organics were washed with H2O, brine
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and evaporation
  6. customfollowed by reverse phase HPLC purification

Sources & evidence

ORD record
ord-cf8efa48e9b5417ab610edb666547600
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

Loading…