Triethylamine → HCID 178456374, compound

HRID 909257Notes

Reaction equation

HRID 909257 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][CH:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[CH3:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]([N:24]2[CH2:25][CH2:26][N:21]([CH:19]([CH3:20])[CH3:18])[CH2:22][CH2:23]2)=[O:17])[CH2:13][CH2:14]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 780131-IsopropylpiperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178453972HCID 178453972, compound

Product 1

HCID 178456374HCID 178456374, compoundYield 107.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3 g (12 mmol) 4-tert-butoxycarbonylamino-trans-cyclohexane carboxylic acid (commercially available), 1.74 g (14 mmol) 1-(2-propyl)-piperazine (commercially available), 4.75 g (15 mmol) TBTU and 3.64 g (36 mmol) NEt3 in 10 ml DMF was stirred for 3 h at room temperature. After evaporation the residue was washed with 1N NaHCO3 solution, extracted with DCM and the combined organic layers dried with MgSO4 and evaporated to dryness to yield 4.56 g (94%) of the title compound. MS (m/e): 354.3 (MH+).

Workup

  1. customAfter evaporation the residue
  2. washwas washed with 1N NaHCO3 solution
  3. extractionextracted with DCM
  4. dry with materialthe combined organic layers dried with MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5469706f48e744b9b5c9bce029331afc
Source dataset
uspto-grants-2011_09
Patent number
US08017773B2

Reaction notes

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