Towards a selective Boc deprotection on acid cleavable Wang resin

Tetrahedron Letters

Volumn 44, Issue 25, 2003, Pages 4757-4759

  Lejeune, Valérie ^a   Martinez, Jean ^a   Cavelier, Florine ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; RESIN; TRIMETHYLSILYL DERIVATIVE; TRIMETHYLSILYLTRIFLATE; UNCLASSIFIED DRUG; WANG RESIN;

ARTICLE; CHEMICAL REACTION; DEPROTECTION REACTION; REACTION TIME;

EID: 0038101555     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00993-6     Document Type: Article

References (15)

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6. 2O (1 mmol, 94.4 μl) and 40 equiv. of TEA (1 mmol, 139.1 μl) in 5 ml of DCM overnight. Then the cleavage was effected with TFA 95% (1.5 ml) for 3 h. The resin was then filtered and washed three times with DCM. The combined filtrates were concentrated and the residue was dissolved in 9 ml of acetonitrile, of which 5 μl were injected in HPLC (analysis at 263 nm).
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12. Deprotection protocol: To a reaction vessel containing 35 mg of resin (22 μmol, according to the loading), were added 2.4 ml of deprotection mixture, freshly prepared from 133.5 μl of TEA, 76.5 μl of TMSOTf and 2.2 ml of DCM. The resin was shaken for 10 min then filtered and washed with 5×2 ml of DCM, 2×2 ml of DIEA 10% in DCM, 3×2 ml of DCE. Deprotection was carried out for another 10 min with a fresh deprotection mixture. The resin was filtered then washed with 5×2 ml of DCM, 2×2 ml of DIEA 10% in DCM, 2×2 ml of DCM and 2×2 ml of DMF. Then 3 ml of methanol were added to the resin and the reaction mixture was sonicated for 30 min. After filtration, the resin was washed with 5×2 ml of DMF and 3×2 ml of DCM.
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