Triethylamine → HCID 86635184, compound

HRID 553560Notes

Reaction equation

HRID 553560 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@:17]([CH3:21])([C:18]([OH:20])=O)[CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:22][CH3:23])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:24][C@@H:25]([CH:42]([CH3:44])[CH3:43])[CH2:26][N:27]1[CH2:32][CH2:31][C@:30]([C:34]2[CH:35]=[C:36]([OH:40])[CH:37]=[CH:38][CH:39]=2)([CH3:33])[C@@H:29]([CH3:41])[CH2:28]1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C1COCC1>[OH:40][C:36]1[CH:35]=[C:34]([C@:30]2([CH3:33])[CH2:31][CH2:32][N:27]([CH2:26][C@@H:25]([NH:24][C:18]([C@@:17]3([CH3:21])[CH2:16][C:15]4[C:10](=[CH:11][C:12]([O:22][CH3:23])=[CH:13][CH:14]=4)[CH2:9][N:8]3[C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])=[O:20])[CH:42]([CH3:43])[CH3:44])[CH2:28][C@@H:29]2[CH3:41])[CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10517637HCID 10517637, compoundHCID 44596878HCID 44596878, compound

Product 1

HCID 86635184HCID 86635184, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 2.8 (200 mg, 0.623 mmol), 3-{(3R,4R)-1-[(2S)-2-amino-3-methylbutyl]-3,4-dimethylpiperidin-4-yl}phenol (J) (181 mg, 0.623 mmol) and BOP reagent (275 mg, 0.623 mmol) were dissolved in THF (20 mL). Triethylamine (1 mL) was added and the solution was stirred at room temperature for 3 h. The solution was extracted with CH2Cl2 and saturated NaHCO3 solution. The organic layer was dried and purified by column chromatography to afford 250 mg, (68%) of 2.9.

Workup

  1. extractionThe solution was extracted with CH2Cl2 and saturated NaHCO3 solution
  2. customThe organic layer was dried
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-e8910d2b8ff844f38b8c20e0837394b9
Source dataset
uspto-grants-2011_11
Patent number
US08048895B2

Reaction notes

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