Triethylamine → HCID 66756585, compound

HRID 855818Notes

Reaction equation

HRID 855818 reaction equation
[CH2:1]([C@@H:3]1[NH:7][C@H:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:5][CH2:4]1)[CH3:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.O.[C:36]([O:40][C:41]([NH:43][C@H:44]([C:49](O)=[O:50])[CH2:45][CH:46]([CH3:48])[CH3:47])=[O:42])([CH3:39])([CH3:38])[CH3:37].C(N(CC)CC)C>CN(C)C=O>[C:36]([O:40][C:41]([NH:43][C@H:44]([C:49]([N:7]1[C@@H:3]([CH2:1][CH3:2])[CH2:4][CH2:5][C@H:6]1[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:50])[CH2:45][CH:46]([CH3:47])[CH3:48])=[O:42])([CH3:38])([CH3:39])[CH3:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 12373896N-Boc-L-Leucine HydrateHCID 66756635HCID 66756635, compound

Product 1

HCID 66756585HCID 66756585, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl(5S)-5-ethyl-L-prolinate (2.5 mmol), 2-(1H-benzotriazol-1yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (1.00 g, 3.13 mmol) and N-(tert-butoxycarbonyl)-L-leucine hydrate (0.779 g, 3.12 mmol) were mixed in 4 mL of dimethylformamide. Triethylamine (approx 1.1 mL) was added until the pH reached about 6 (wet pH paper). After stirring for 16 hours, the mixture was concentrated under reduced pressure and the residue partitioned between 1 N HCl and ethyl acetate. The organic layer was washed with saturated NaHCO3, dried (Na2SO4), filtered, concentrated under reduced pressure and purified by flash chromatography (30% to 50% ethyl acetate/hexane) to provide the titled compound. MS (ESI) m/z 385 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customthe residue partitioned between 1 N HCl and ethyl acetate
  3. washThe organic layer was washed with saturated NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by flash chromatography (30% to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0698cc450de34e438cd5035f8ac3bdf6
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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