Diisopropylethylamine → Trifluoroacetic acid

HRID 1920552Notes

Reaction equation

HRID 1920552 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

Alternatively, 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 (0.053 ml, 0.306 mmol), HATU (0.058 g, 0.153 mmol) and 5,6-Diethyl-indan-2-ylamine hydrochloride (0.035 g, 0.153 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-9c4b633503f84b779ab56bdf5158a4dd
Source dataset
uspto-grants-2012_05
Patent number
US08168654B2

Reaction notes

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