Triethylamine → Ammonia

HRID 52575Notes

Reaction equation

HRID 52575 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:2]([C:13]([OH:15])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:12])[NH:8][N+:9]([O-:11])=[O:10].Cl.[NH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1.C([N:36](CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(#N)C>[C:19]([O:18][C:16]([NH:1][C@@H:2]([C:13]([NH:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)=[O:15])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH2:12])=[N:8][N+:9]([O-:11])=[O:10])=[O:17])([CH3:22])([CH3:21])[CH3:20].[NH3:36]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 66449Tyramine hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178454201HCID 178454201, compound

Product 2

HCID 222AmmoniaHCID 136381088HCID 136381088, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1.0 g (3.13 Mol) of Boc-D-Arg(NO2)-OH, 0.57 g (3.28 mMol) of tyramine-hydrochloride, 0.91 ml (0.66 g =6.53 mMol) of triethylamine and 20 ml of anhydrous acetonitrile were added 1.05 g (3.27 mMol) of TBTU, with stirring and external cooling with ice water. The mixture was allowed to come up to ambient temperature and stirring was continued overnight under these conditions. The precipitate was filtered off, the filtrate was evaporated down in vacuo, the residue was distributed between water and ethyl acetate. The ethyl acetate phase was then purified by column chromatography on silica gel (Macherey-Nagel, 35-70 mesh ASTM) using dichloromethane/methanol/cyclohexane/conc. aqueous ammonia =68/15/15/2 (v/v/v/v). 0.8 g (58% of theory) of the title compound were obtained in the form of an amorphous foam, Rf 0.49 (Macherey-Nagel Polygram® SIL G/UV254, ready-made films for TLC; eluant: dichloromethane/methanol/cyclohexane/conc. aqueous ammonia =68/15/15/2 (v/v/v/v)).

Workup

  1. customto come up to ambient temperature
  2. stirringstirring
  3. filtrationThe precipitate was filtered off
  4. customthe filtrate was evaporated down in vacuo
  5. customThe ethyl acetate phase was then purified by column chromatography on silica gel (Macherey-Nagel, 35-70 mesh ASTM)

Sources & evidence

ORD record
ord-2f581446dccc4df89ac08939b0a8b4ad
Source dataset
uspto-grants-1997_04
Patent number
US05616620

Reaction notes

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