Triethylamine → HCID 66666644, compound

HRID 1617979Notes

Reaction equation

HRID 1617979 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:33])[CH2:9][C@H:10]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][CH:27]([C:30](O)=[O:31])[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.Cl.[NH2:64][CH2:65][C:66]([O:68][CH3:69])=[O:67]>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:33])[CH2:9][C@H:10]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][CH:27]([C:30]([NH:64][CH2:65][C:66]([O:68][CH3:69])=[O:67])=[O:31])[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66666008HCID 66666008, compound

Product 1

HCID 66666644HCID 66666644, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (R)-1-(4-(3-(2-methylpyridin-4-yl)-3-oxo-1-o-tolylpropyl)phenyl)-piperidine-4-carboxylic acid (example 367, step 1; 100 mg, 226 μmol) triethylamine (68.6 mg, 94.5 μl, 678 μmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (79.8 mg, 249 μmol) in tetrahydrofuran (5 mL) was stirred at room temperature for 15 min, then treated with methyl 2-aminoacetate hydrochloride (42.6 mg, 339 μmol). The reaction mixture was stirred for 20 h at room temperature, then partitioned between sat. aq. ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated to afford the crude title compound (130 mg), which was directly used in the next step. Yellow oil, MS (ESI+): m/z=514.6 ([M+H]+).

Workup

  1. stirringThe reaction mixture was stirred for 20 h at room temperature
  2. custompartitioned between sat. aq. ammonium chloride solution and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-58acf20301c44b9abf3b92c947cc4ffc
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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