Sodium Hydroxide → 3-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)propanoic acid

HRID 2040707Notes

Reaction equation

HRID 2040707 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([CH2:21][N:22]([CH3:34])[CH:23]2[CH2:26][CH:25]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[CH2:24]2)[O:12]1.[OH-].[Na+]>CO>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([CH2:21][N:22]([CH3:34])[CH:23]2[CH2:26][CH:25]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:24]2)[O:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67774466ethyl 3-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)propanoate

Product 1

HCID 677751233-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of ethyl 3-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)propanoate (0.39 g, 0.82 mmol) in methanol (14 mL) was treated with a 1 M aqueous solution of sodium hydroxide (1.56 mL, 1.56 mmol) and the reaction mixture was heated at 50° C. with stirring for 3.5 h; HPLC/LC MS indicated conversion to the desired product. The reaction mixture was concentrated in vacuo and the aqueous residue was diluted with water (10 mL) and extracted with CH2Cl2 (3×5 mL). The aqueous layer was treated with a 1 M aqueous solution of hydrogen chloride (1.44 mL, 1.44 mmol) to adjust to pH 7. The clear, colorless solution was lyophilized to afford the crude title compound (0.487 g, 110%) as a slightly off-white solid, yield accounts for 1.56 mmol NaCl (91 mg): MS (ESI+) for C21H30N6O5 m/z 447.1 (M+H)+; MS (ESI−) for C21H30N6O5 m/z 445.2 (M−H)−; HPLC purity >95% (ret. time, 1.949 min).

Sources & evidence

ORD record
ord-732fdd04fdcb45c49791977553391746
Source dataset
uspto-grants-2013_11
Patent number
US08580762B2

Reaction notes

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