N,N-Diethylethanamine trihydrofluoride → HCID 68546370, compound

HRID 2250408Notes

Reaction equation

HRID 2250408 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:44][Si](C(C)(C)C)(C)C)[CH2:21][NH:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:33]=[C:34]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:35]=[CH:36][CH:37]=3)=[CH:27][CH:26]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F.F.F.C(N(CC)CC)C>O1CCCC1.[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:44])[CH2:21][NH:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:33]=[C:34]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:35]=[CH:36][CH:37]=3)=[CH:27][CH:26]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 68544142HCID 68544142, compound

Product 1

HCID 68546370HCID 68546370, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

The product of step (d) (275 mg) and triethylamine trihydrofluoride (1.0 mL) in tetrahydrofuran (10 mL) was stirred at room temperature for 16 h. The solution was diluted with sodium hydroxide (0.5M, 10 mL), extracted with dichloromethane (2×10 mL) and the combined organics dried over sodium sulfate and evaporated to afford the title intermediate (105 mg), which was used directly in the next step without further purification.

Workup

  1. extractionextracted with dichloromethane (2×10 mL)
  2. dry with materialthe combined organics dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-2d29246e938d4ec3b9d1798550e319cc
Source dataset
uspto-grants-2008_01
Patent number
US07317023B2

Reaction notes

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