Diisopropylethylamine → Trifluoroacetic acid

HRID 1920551Notes

Reaction equation

HRID 1920551 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[C:8]([CH2:11][N+:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C@@H:14]([O:20][C:21](=[O:36])[C:22]([OH:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:13]2)([OH:10])=O.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH2:71]([C:73]1[CH:74]=[C:75]2[C:79](=[CH:80][C:81]=1[CH2:82][CH3:83])[CH2:78][CH:77]([NH2:84])[CH2:76]2)[CH3:72]>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[CH2:82]([C:81]1[CH:80]=[C:79]2[C:75](=[CH:74][C:73]=1[CH2:71][CH3:72])[CH2:76][CH:77]([NH:84][C:8]([CH2:11][N+:12]13[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19]1)[CH:14]([O:20][C:21](=[O:36])[C:22]([OH:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:13]3)=[O:10])[CH2:78]2)[CH3:83]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 102361265,6-diethyl-2,3-dihydro-1H-inden-2-amine HydrochlorideHCID 86611356(R)-1-Carboxymethyl-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]-octane trifluoroacetate

Product 2

HCID 6422Trifluoroacetic acidHCID 86639172HCID 86639172, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of (R)-1-carboxymethyl-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]octane trifluoroacetate [Ex. 62] (0.052 g, 0.102 mmol) in dry DMF (5 ml) is added DIPEA (0.070 ml, 0.408 mmol), HATU (0.097 g, 0.255 mmol) and 5,6-Diethyl-indan-2-ylamine hydrochloride (0.058 g, 0.255 mmol). The mixture is left to stir at room temperature overnight. The solvent is removed in vacuo and purification by mass directed preparative HPLC eluting with acetonitrile:water:trifluoroacetic acid yields the titled compound.

Workup

  1. waitThe mixture is left
  2. customThe solvent is removed in vacuo and purification by mass
  3. washeluting with acetonitrile

Sources & evidence

ORD record
ord-c1c0347ae59249a297c783f5877baa0c
Source dataset
uspto-grants-2012_05
Patent number
US08168654B2

Reaction notes

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