N,N-Diethylethanamine trihydrofluoride → HCID 178493267, compound

HRID 630408Notes

Reaction equation

HRID 630408 reaction equation
[OH:1][C:2]([C:43]1[S:44][CH:45]=[CH:46][CH:47]=1)([C:38]1[S:39][CH:40]=[CH:41][CH:42]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]([CH2:14][CH2:15][CH2:16][C:17]([NH:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([CH2:28][O:29][Si](C(C)(C)C)(C)C)=[CH:22][C:21]=2[Cl:37])=[O:18])[CH3:13])[CH2:8][CH2:7]1)=[O:4].F.F.F.C(N(CC)CC)C>O1CCCC1>[OH:1][C:2]([C:38]1[S:39][CH:40]=[CH:41][CH:42]=1)([C:43]1[S:44][CH:45]=[CH:46][CH:47]=1)[C:3]([O:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([N:12]([CH2:14][CH2:15][CH2:16][C:17]([NH:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([CH2:28][OH:29])=[CH:22][C:21]=2[Cl:37])=[O:18])[CH3:13])[CH2:10][CH2:11]1)=[O:4]

Participants

4

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 178493268HCID 178493268, compound2×

Product 1

HCID 178493267HCID 178493267, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-4-[(4-{[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyphenyl]amino}-4-oxobutyl)(methyl)amino]cyclohexyl hydroxy(di-2-thienyl)-acetate (intermediate 84; 90 mg, 0.12 mmol) in tetrahydrofuran (3.5 mL) was added triethylamine trihydrofluoride (0.55 mL, 5.46 mmol). The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the crude obtained was purified by preparative reversed-phase HPLC (System 2), to give the title compound (23%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude obtained
  3. customwas purified by preparative reversed-phase HPLC (System 2)

Sources & evidence

ORD record
ord-d708c383a30c43668d5e172e9333030b
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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