Diisopropylethylamine → HCID 178462118, compound

HRID 1944713Notes

Reaction equation

HRID 1944713 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].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[F:51][C:52]1[CH:57]=[CH:56][C:55]([C@H:58]([NH2:60])[CH3:59])=[CH:54][CH:53]=1>C1COCC1>[F:51][C:52]1[CH:57]=[CH:56][C:55]([C@H:58]([NH:60][C:15]([C@H:12]2[CH2:11][CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:14][CH2:13]2)=[O:17])[CH3:59])=[CH:54][CH:53]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6950187(1R)-(+)-1-(4-Fluorophenyl)ethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178453972HCID 178453972, compound

Product 1

HCID 178462118HCID 178462118, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trans-4-(tert-Butoxycabonylamino)cyclohexanecarboxylic acid (10.2 g, 42 mmol), HATU (24 g, 63 mmol) and N,N-diisopropylethylamine (22 ml, 126 mmol) were dissolved in THF (350 ml). The reaction mixture was stirred for 30 min at room temperature, then (R)-1-(4-Fluoro-phenyl)-ethylamine 6.3 ml, 46 mmol) was added. The reaction was stirred overnight at room temperature. LCMS indicated that the reaction was complete, and it was concentrated in vacuo. The concentrate was taken up in 1M NaOH (500 ml) and EtOAc (100 ml) and was stirred for 1 hr. The precipitate that formed was collected by filtration and washed with 1M NaOH:EtOAc (4:1) and dried to give the title compound as a white solid (14.8 g, 97%). LCMS [M+H]=365.3

Workup

  1. stirringThe reaction was stirred overnight at room temperature
  2. concentrationit was concentrated in vacuo
  3. stirringEtOAc (100 ml) and was stirred for 1 hr
  4. customThe precipitate that formed
  5. filtrationwas collected by filtration
  6. washwashed with 1M NaOH:EtOAc (4:1)
  7. customdried

Sources & evidence

ORD record
ord-feea76296de04459aa1a40392af0aa91
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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