Triethylamine → HCID 178456387, compound

HRID 1984020Notes

Reaction equation

HRID 1984020 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.[CH:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:13])[CH3:12].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[CH:11]([N:14]1[CH2:19][CH2:18][N:17]([C:8]([C@H:5]2[CH2:4][CH2:3][C@@H:2]([OH:1])[CH2:7][CH2:6]2)=[O:10])[CH2:16][CH2:15]1)([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 780131-IsopropylpiperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178525779HCID 178525779, compound

Product 1

HCID 178456387HCID 178456387, compoundYield 120.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 428 mg (3.0 mmol) of cis-4-hydroxycyclohexanecarboxylic acid (commercially available), 318 mg (1.5 mmol) of 1-(isopropyl)-piperazine (commercially available), 1.14 g (3.6 mmol) of TBTU and 900 mg (9 mmol) of triethylamine in 3 ml DMF was stirred for 12 h at room temperature. The mixture was purified by column chromatography on silica eluting with CH2Cl2 and methanol=9:1. Evaporation of the combined product fractions yielded 460 mg (61%) of the title compound as light brown oil. MS (m/e): 255.2 (MH+).

Workup

  1. customThe mixture was purified by column chromatography on silica eluting with CH2Cl2 and methanol=9:1
  2. customEvaporation of the combined product fractions

Sources & evidence

ORD record
ord-65e1c6c36ddc44a5b92ed7e47adf12f5
Source dataset
uspto-grants-2009_06
Patent number
US07544683B2

Reaction notes

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