Benzyl 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)(ethyl)amino)cyclobutyl)propanoate → HCID 67775307, compound

HRID 511690Notes

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]([CH2:39][CH3:40])[CH:23]2[CH2:26][CH:25]([CH2:27][CH2:28][C:29]([O:31]CC3C=CC=CC=3)=[O:30])[CH2:24]2)[O:12]1>CO.[Pd]>[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]([CH2:39][CH3:40])[CH:23]2[CH2:26][CH:25]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:24]2)[O:12]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of Benzyl 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)(ethyl)amino)cyclobutyl)propanoate (2.6 g, 4.73 mmol) in MeOH (40 mL) was added 10% Pd/C (2.3 g) and the mixture was stirred under H2 atmosphere at 50° C. for 20 h. The mixture was filtered and the filtrate was concentrated to obtain the target (2 g, yield: 92%) as a white solid. 1H NMR (500 MHz, MeOD): δH 8.27 (s, 1H), 8.25 (s, 1H), 6.30 (s, 1H), 5.52-5.49 (m, 1H), 5.14-5.12 (m, 1H), 4.51-4.47 (m, 1H), 3.43-3.36 (m, 2H), 3.22-3.15 (m, 1H), 2.94-2.89 (m, 2H), 2.28-2.05 (m, 4H), 1.96-1.80 (m, 2H), 1.74-1.69 (m, 1H), 1.65-1.59 (m, 5H), 1.41-1.36 (m, 4H), 1.03-0.99 (m, 3H) ppm; ESI-MS (m/z): 461.3 [M+1]+.

Workup

filtrationThe mixture was filtered
concentrationthe filtrate was concentrated
customto obtain the target (2 g, yield: 92%) as a white solid

Sources & evidence

ORD record: ord-d583b600139b46519c94e72d67485dca
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096634B2

Reaction notes

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