Ethyl Acetate → HCID 86632276, compound

HRID 561983Notes

Reaction equation

HRID 561983 reaction equation
[NH2:1][CH:2]([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[CH:35][CH:34]=1)[C:3]([NH:5][C@H:6]([C:15]1[NH:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[C:27][Si](C)(C)C)=[CH:22][C:21]=2[F:32])=[CH:18][N:19]=1)[C@H:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O1CCCC1>[NH2:1][CH:2]([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][O:42][C:43]([CH3:44])([CH3:46])[CH3:45])=[CH:35][CH:34]=1)[C:3]([NH:5][C@H:6]([C:15]1[NH:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[CH:27])=[CH:22][C:21]=2[F:32])=[CH:18][N:19]=1)[C@H:7]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:8])=[O:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 67001290HCID 67001290, compound

Product 1

HCID 86632276HCID 86632276, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-amino-2-[4-(2-tert-butoxy-ethoxy)-phenyl]-N-{(1S,2S)-1-[5-(2-fluoro-4-trimethylsilanylethynyl-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-acetamide (290 mg, 0.45 mmol) in tetrahydrofuran (10 mL) at room temperature under an atmosphere of nitrogen was added 1.0 M tetrabutylammonium fluoride in tetrahydrofuran (680 μL, 0.68 mmol) and the resulting solution was allowed to stir for 2 hours. The reaction was poured into ethyl acetate (50 mL), washed with water (2×20 mL), brine, dried over sodium sulfate, filtered and concentrated in vacuo to give 2-amino-2-[4-(2-tert-butoxy-ethoxy)-phenyl]-N-{(1S,2S)-1-[5-(4-ethynyl-2-fluoro-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-acetamide which was used without further purification (250 mg, 97%).

Workup

  1. washwashed with water (2×20 mL), brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-578918efad04400091f2b9c520013f70
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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