Triethylamine → HCID 68711084, compound

HRID 638806Notes

Reaction equation

HRID 638806 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.C[NH2+]C.[Cl:30][C:31]1[CH:32]=[C:33]([CH:41]=[CH:42][C:43]=1[Cl:44])[CH2:34][N:35]1[CH2:38][CH:37]([CH2:39][NH2:40])[CH2:36]1>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:12])[NH:40][CH2:39][CH:37]1[CH2:38][N:35]([CH2:34][C:33]2[CH:41]=[CH:42][C:43]([Cl:44])=[C:31]([Cl:30])[CH:32]=2)[CH2:36]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 18551499Dimethyl-ammonium hexafluorophosphateHCID 68712490HCID 68712490, compound

Product 1

HCID 68711084HCID 68711084, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-Butoxycarbonylamino-acetic acid (1.88 g, 10.7 mmol) in dichloromethane (15 ml) is treated with triethylamine (1.5 ml, 10.7 mmol) and [Dimethylamino-[1,2,3]-triazolo-[4,5-b]pyridin-3-yloxy)-methylene]-dimethyl-ammonium hexafluoro phosphate (4.06 g, 10.7 mmol) and stirred for 5 minutes. To the reaction mixture is added a solution of C-[1-(3,4-Dichloro-benzyl)-azetidin-3-yl]-methylamine (2.64 g, 10.7 mmol) in dichloromethane (15 ml) with stirring for a further 3 hours. The reaction mixture is partitioned between dichloromethane and saturated sodium bicarbonate solution, the organic phase is washed with brine, dried over magnesium sulphate and evaporated. The crude product is purified by chromatography over flash silica eluting with 7% methanol in dichloromethane to afford the title compound.

Workup

  1. stirringwith stirring for a further 3 hours
  2. customThe reaction mixture is partitioned between dichloromethane and saturated sodium bicarbonate solution
  3. washthe organic phase is washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe crude product is purified by chromatography over flash silica eluting with 7% methanol in dichloromethane

Sources & evidence

ORD record
ord-8c20a0d7fbad47a681ab0069aaa0dfa2
Source dataset
uspto-grants-2010_04
Patent number
US07691841B2

Reaction notes

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