Benzoic acid 5-(6-benzoylamino-purin-9-yl)-4-fluoro-2-trityloxymethyl-tetrahydro-furan-3-yl ester → Benzoic acid 5-(6-benzoylamino-purin-9-yl)-4-fluoro-2-hydroxymethyl-tetrahydro-furan-3-yl ester

HRID 2191068Notes

Reaction equation

[C:1]([NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[CH:19]1[O:23][CH:22]([CH2:24][O:25]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:21]([O:45][C:46](=[O:53])[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:20]1[F:54])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O>[C:1]([NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[CH:19]1[O:23][CH:22]([CH2:24][OH:25])[CH:21]([O:45][C:46](=[O:53])[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:20]1[F:54])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Compound 55.3 (13.0 g, 17.4 mmol) was treated with 80% AcOH (100 mL) and stirred at 40° C. for 5 h. The solvent was removed in vacuo and the mixture was subjected to Combiflash purification (SiO2, 330 g, 0-100% EtOAc-hexanes gradient) which afforded 55.4 as a white solid (4.72 g, 45%).

Workup

customThe solvent was removed in vacuo
custompurification (SiO2, 330 g, 0-100% EtOAc-hexanes gradient) which

Sources & evidence

ORD record: ord-c1638f80f4c64d86a1412653eda7d954
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324179B2

Reaction notes

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