Diisopropylethylamine → HCID 178520989, compound

HRID 1984015Notes

Reaction equation

HRID 1984015 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.[CH3:33][CH2:34][N:35](C(C)C)[CH:36](C)[CH3:37]>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])[CH2:34][CH2:33]2)[CH2:22][CH2:23][CH2:24]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178525779HCID 178525779, compound

Product 1

HCID 178520989HCID 178520989, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 214 mg (1.5 mmol) of cis-4-hydroxycyclohexanecarboxylic acid (commercially available), 316 mg (1.5 mmol) of 1-(2-cyclobutyl)-piperazine dihydrogen chloride (WO 2004101546), 572 mg (1.8 mmol) of TBTU and 751 mg (7.4 mmol) of DIPEA in 5 ml DMF was stirred for 8 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 silica eluting with CH2Cl2 and methanol=9:1. Evaporation of the combined product fractions yielded 300 mg (76%) 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 silica eluting with CH2Cl2 and methanol=9:1
  4. customEvaporation of the combined product fractions

Sources & evidence

ORD record
ord-6370a15784444dfca63057527d07387d
Source dataset
uspto-grants-2009_06
Patent number
US07544683B2

Reaction notes

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