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

HRID 2191067Notes

Reaction equation

HRID 2191067 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[CH:11]1[O:15][CH:14]([CH2:16][O:17][C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]([OH:37])[CH:12]1[F:38].[C:39](Cl)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:40]>N1C=CC=CC=1>[C:39]([NH:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[O:15][CH:14]([CH2:16][O:17][C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:13]([O:37][C:18](=[O:17])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]1[F:38])(=[O:40])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 68594081HCID 68594081, compound

Product 1

HCID 86641135Benzoic acid 5-(6-benzoylamino-purin-9-yl)-4-fluoro-2-trityloxymethyl-tetrahydro-furan-3-yl esterYield 198.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 55.2 (18.2 mmol) in pyridine (180 mL) was treated with BzCl (6.33 mL, 54.6 mmol) and stirred overnight. The solvent was removed in vacuo and the solid was dissolved in EtOAc (100 mL) and washed with H2O (2×50 mL). The solution was dried over MgSO4, filtered, and subjected to Combiflash purification (SiO2, 330 g, 0-100% EtOAc-hexanes gradient) which afforded 55.3 as a white solid (13.0 g, 96%, two steps).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe solid was dissolved in EtOAc (100 mL)
  3. washwashed with H2O (2×50 mL)
  4. dry with materialThe solution was dried over MgSO4
  5. filtrationfiltered
  6. custompurification (SiO2, 330 g, 0-100% EtOAc-hexanes gradient) which

Sources & evidence

ORD record
ord-3beb626a782a4fd790fcdb88dce83e7c
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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