Triethylamine → HCID 86591771, compound

HRID 1062685Notes

Reaction equation

HRID 1062685 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([OH:20])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH3:53][O:54][C:55](=[O:64])[C@@H:56]1[CH2:60][C@H:59]([N:61]=[N+:62]=[N-:63])[CH2:58][NH:57]1>CN(C=O)C.O.C(OCC)(=O)C>[CH3:53][O:54][C:55](=[O:64])[C@@H:56]1[CH2:60][CH:59]([N:61]=[N+:62]=[N-:63])[CH2:58][N:57]1[C:18](=[O:20])[CH2:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222827343-(4-{[(tert-Butoxycarbonyl)amino]methyl}phenyl)propanoic acid2×HCID 86594240HCID 86594240, compound

Product 1

HCID 86591771HCID 86591771, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.70 g (9.5 mmol) of 3-(4-tert-butyloxycarbonylaminomethylphenyl)propionic acid (starting compound A6) are dissolved in 40 ml of DMF, and 2.7 ml of triethylamine are added. After stirring for 5 min., 3.63 g of HBTU are added and, after a further 5 min., 2 g of (2S,4S)-4-azidoproline methyl ester hydrochloride. Stirring at RT overnight is followed by addition of ethyl acetate and water and separation of the phases. 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. 4.1 g of the title compound are obtained as a pale orange oil. The mass spectrum shows the molecular peak MNH4+ at 449 Da.

Workup

  1. stirringStirring at RT overnight
  2. washThe organic phase is washed once each with 1N sodium hydroxide solution, 1N hydrochloric acid solution, saturated sodium bicarbonate solution and saturated brine
  3. dry with materialDrying over magnesium sulfate
  4. concentrationis followed by concentration
  5. customdrying under high vacuum

Sources & evidence

ORD record
ord-0db9fc1e380045ea8d353909bce84b4d
Source dataset
uspto-grants-2005_11
Patent number
US06962941B2

Reaction notes

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