Triethylamine → HCID 15609251, compound

HRID 642929Notes

Reaction equation

HRID 642929 reaction equation
[O:1]=[C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][N:3]1[CH:9]1[O:31][CH:12]2[CH2:13][O:14][Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)[O:18][CH:11]2[CH:10]1[O:32][C:33](=[O:35])[CH3:34].C(N(CC)CC)C.F.F.F.C(N(CC)CC)C>ClCCl>[O:1]=[C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][N:3]1[CH:9]1[CH:10]([O:32][C:33](=[O:35])[CH3:34])[CH:11]([OH:18])[CH:12]([CH2:13][OH:14])[O:31]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 66774323HCID 66774323, compound

Product 1

HCID 15609251HCID 15609251, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The Tips protecting group is removed from Compound 5 as illustrated in the literature (Protective Groups in Organic Synthesis, 3rd edition, 1999, pp. 239 and references therein, Greene, T. W. and Wuts, P. G. M., eds, Wiley-Interscience, New York). To a solution of 5 (1 eq.) in anhydrous dichloromethane is added triethylamine (2 eq.) and triethylamine trihydrofluoride (2 eq.). The reaction mixture is monitored by thin layer chromatography until complete at which point the reaction mixture is diluted with additional dichloromethane, washed with aqueous NaHCO3, dried over anhydrous Na2SO4, and evaporated. The resulting Compound 6 is optionally purified by silica gel chromatography.

Workup

  1. customis removed from Compound 5
  2. customin Organic Synthesis, 3rd edition, 1999
  3. washwashed with aqueous NaHCO3
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated
  6. customThe resulting Compound 6 is optionally purified by silica gel chromatography

Sources & evidence

ORD record
ord-0bd79e3bcfa6427a946d05dd943a8e0b
Source dataset
uspto-grants-2010_04
Patent number
US07696345B2

Reaction notes

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