Triethylamine → 2-[2-(3,5-Difluoro-benzylcarbamoyl)-propionylamino]-3-(1H-indol-3-yl)-propionic acid tert-butyl ester

HRID 2223249Notes

Reaction equation

HRID 2223249 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([F:17])[CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[CH:8]([CH3:12])[C:9]([OH:11])=O.Cl.[C:19]([O:23][C:24](=[O:37])[C@H:25]([CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)[NH2:26])([CH3:22])([CH3:21])[CH3:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[C:19]([O:23][C:24](=[O:37])[CH:25]([NH:26][C:9](=[O:11])[CH:8]([C:7](=[O:13])[NH:6][CH2:5][C:4]1[CH:14]=[C:15]([F:17])[CH:16]=[C:2]([F:1])[CH:3]=1)[CH3:12])[CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11514895(S)-tert-butyl 2-amino-3-(1H-indol-3-yl)propanoate hydrochlorideHCID 21091473N-(3,5-difluoro-benzyl)-2-methyl-malonamic acid

Product 1

HCID 692836102-[2-(3,5-Difluoro-benzylcarbamoyl)-propionylamino]-3-(1H-indol-3-yl)-propionic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-(3,5-Difluoro-benzyl)-2-methyl-malonamic acid (3.00 g, 12.3 mmol), L-tryptophan-tert-butylester hydrochloride (3.66 g, 12.3 mmol), TBTU (O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium-tetrafluoroborate, 3.96 g, 12.3 mmol) and triethylamin (3.74 g, 3.70 mmol) were dissolved in DMF (15 ml) and stirred for 5 h at r.t. The reaction mixture was poured into water and the product mixture was extracted with ethyl acetate. The organic layers were dried (Na2SO4). After evaporation of the solvent, the title compound, MS: m/e=486.4 (M+H+), (6.45 g, quant.) was obtained by chromatographic purification of the residue (silica gel, MeOH, CH2Cl2).

Workup

  1. extractionthe product mixture was extracted with ethyl acetate
  2. dry with materialThe organic layers were dried (Na2SO4)
  3. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-f9af4bff7cd243e6b0e6963277ceaea3
Source dataset
uspto-grants-2008_05
Patent number
US07375099B2

Reaction notes

Loading…