Triethylamine → HCID 178520990, compound

HRID 1984017Notes

Reaction equation

HRID 1984017 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.CN(C(ON1N=[N:26][C:21]2[CH:22]=[CH:23][CH:24]=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:33]([N:35](CC)[CH2:36][CH3:37])[CH3:34]>CN(C=O)C.C(OCC)(=O)C>[CH:21]1([N:26]2[CH2:37][CH2:36][N:35]([C:8]([C@H:5]3[CH2:4][CH2:3][C@H:2]([OH:1])[CH2:7][CH2:6]3)=[O:10])[CH2:33][CH2:34]2)[CH2:22][CH2:23][CH2:24]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178525779HCID 178525779, compound

Product 1

HCID 178520990HCID 178520990, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 500 mg (3.5 mmol) of cis-4-hydroxycyclohexanecarboxylic acid (commercially available), 739 mg (3.5 mmol) of 1-(2-cyclobutyl)-piperazine dihydrogen chloride (WO 2004101546), 1.23 g (3.8 mmol) of TBTU and 1.40 g (13.8 mmol) of triethylamine in 7 ml DMF was stirred for 12 h at room temperature. The mixture was diluted with ethyl acetate, washed with water and brine, and evaporated. The residue was purified by column chromatography on NH2-silica gel eluting with CH2Cl2 and methanol=from 100:0 to 98:2. Evaporation of the combined product fractions yielded 600 mg (65%) of the title compound as light brown oil. MS (m/e): 267.1 (MH+).

Workup

  1. washwashed with water and brine
  2. customevaporated
  3. customThe residue was purified by column chromatography on NH2-silica gel eluting with CH2Cl2 and methanol=from 100:0 to 98:2
  4. customEvaporation of the combined product fractions

Sources & evidence

ORD record
ord-1b19d6781fdc4ffba5e8301700ebf063
Source dataset
uspto-grants-2009_06
Patent number
US07544683B2

Reaction notes

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