Acetic Anhydride → 3'-Acetylamino-5'-O-trityl-2',3'-dideoxyuridine

HRID 1818672Notes

Reaction equation

HRID 1818672 reaction equation
[NH2:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:5][C@@H:4]([N:28]2[CH:35]=[CH:34][C:32](=[O:33])[NH:31][C:29]2=[O:30])[CH2:3]1.[C:36](OC(=O)C)(=[O:38])[CH3:37].C(N(CC)CC)C>C(Cl)Cl>[C:36]([NH:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:5][C@@H:4]([N:28]2[CH:35]=[CH:34][C:32](=[O:33])[NH:31][C:29]2=[O:30])[CH2:3]1)(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 529147963'-Amino-5'-O-trityl-2',3'-dideoxyuridine

Product 1

HCID 687009443'-Acetylamino-5'-O-trityl-2',3'-dideoxyuridineYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 31 (0.10 g, 0.213 mmol) was suspended in DCM (5 ml), and to this was added acetic anhydride (0.047 g, 0.044 ml, 0.469 mmol) and triethylamine (0.065 ml, 0.469 mmol). The mixture was stirred at room temperature for 3 hours. After this time the solvent was evaporated to give a white solid. The product was purified by column chromatography (MeOH/DCM 2%→6%), and evaporation of the solvent gave the title compound as a white solid (0.103 g, 95%).

Workup

  1. customAfter this time the solvent was evaporated
  2. customto give a white solid
  3. customThe product was purified by column chromatography (MeOH/DCM 2%→6%), and evaporation of the solvent

Sources & evidence

ORD record
ord-a1be34db2005473698e495d3e22541bf
Source dataset
uspto-grants-2009_10
Patent number
US07601702B2

Reaction notes

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