Diisopropylethylamine → HCID 86594241, compound

HRID 1062687Notes

Reaction equation

HRID 1062687 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][C:18]([OH:20])=O)[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH3:55][O:56][C:57](=[O:66])[C@@H:58]1[CH2:62][C@H:61]([N:63]=[N+:64]=[N-:65])[CH2:60][NH:59]1>C(Cl)Cl.O.C(OCC)(=O)C>[CH3:55][O:56][C:57](=[O:66])[C@@H:58]1[CH2:62][CH:61]([N:63]=[N+:64]=[N-:65])[CH2:60][N:59]1[C:18](=[O:20])[CH2:17][CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:11]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222827283-(3-{[(tert-Butoxycarbonyl)amino]methyl}phenyl)propanoic acidHCID 86594240HCID 86594240, compound

Product 1

HCID 86594241HCID 86594241, compoundYield 72.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.61 g (5.7 mmol) of 3-(3-tert-butyloxycarbonylaminomethylphenyl)propionic acid (starting compound A11) are dissolved in 14 ml of CH2Cl2, and 2.1 ml of DIPEA are added. After stirring for 5 min., 2.2 g (5.7 mmol) of HBTU are added and, after a further 5 min., 1.0 g (4.8 mmol) of (2S,4S)-4-azidoproline methyl ester hydrochloride. After stirring at RT overnight, ethyl acetate and water are added and the phases are separated. The organic phase is washed once each with 1N sodium hydroxide solution,1N hydrochloric acid solution, saturated sodium bicarbonate solution and saturated brine. Drying over magnesium sulfate is followed by concentration and drying under high vacuum. Further purification takes place by chromatography [Tol/Ac (8:2)] on a silica gel column. The title compound (1.5 g) is obtained as a colorless oil. TLC, silica gel (glass plates), [toluene/acetone (8:2)], Rf=0.31. The mass spectrum shows the molecular peak MNH4+ at 449 Da.

Workup

  1. stirringAfter stirring at RT overnight
  2. customthe phases are separated
  3. washThe organic phase is washed once each with 1N sodium hydroxide solution,1N hydrochloric acid solution, saturated sodium bicarbonate solution and saturated brine
  4. dry with materialDrying over magnesium sulfate
  5. concentrationis followed by concentration
  6. customdrying under high vacuum
  7. customFurther purification

Sources & evidence

ORD record
ord-a895ef61c5ca45b7a366a467082b941d
Source dataset
uspto-grants-2005_11
Patent number
US06962941B2

Reaction notes

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