Triethylamine → HCID 66957928, compound

HRID 1842359Notes

Reaction equation

HRID 1842359 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([O:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=[N:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(CC)CC.[OH:43][CH:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1>CN(C=O)C>[OH:43][CH:44]1[CH2:49][CH2:48][N:47]([C:11](=[O:13])[CH2:10][O:9][C:6]2[C:7](=[O:8])[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=2)[CH2:46][CH2:45]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66957914HCID 66957914, compound

Product 1

HCID 66957928HCID 66957928, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

11.1 g (60.2 mmoles) of intermediate 4i are placed in 250 mL of DMF under nitrogen. At 0° C., 21.3 g (66.3 mmoles) of TBTU then 16.8 mL (120 mmoles) of Et3N then 6.1 g (60.2 mmoles) of 4-hydroxypiperidine are added. The reaction medium is agitated for 20 h at ambient temperature then concentrated to dryness. The residue obtained is purified by silica gel flash chromatography (CH2Cl2-MeOH, gradient 100:0 to 90:10 in 40 min). 10.14 g of intermediate 5c are thus obtained in the form of a yellow solid (yield 63%). TLC silica gel 60 F 254 Merck, CH2Cl2-MeOH: 80:20, Rf=0.59.

Workup

  1. concentrationthen concentrated to dryness
  2. customThe residue obtained
  3. customis purified by silica gel flash chromatography (CH2Cl2-MeOH, gradient 100:0 to 90:10 in 40 min)

Sources & evidence

ORD record
ord-c538460249714c2183a4c9005181ca13
Source dataset
uspto-grants-2015_02
Patent number
US08946225B2

Reaction notes

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