Taurine → HCID 178512541, compound

HRID 1486911Notes

Reaction equation

HRID 1486911 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:52])[CH2:14][C:15]1([CH2:44][C:45](=[O:51])[O:46]C(C)(C)C)[O:19][N:18]=[C:17]([C:20]2[CH:25]=[C:24]([O:26][C:27](=[O:38])[C:28]3[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH2:37])=[NH:36])=[CH:30][CH:29]=3)[CH:23]=[CH:22][C:21]=2[CH2:39][CH2:40][C:41]([OH:43])=O)[CH2:16]1)(C)(C)C.[NH2:53][CH2:54][CH2:55][S:56]([OH:59])(=[O:58])=[O:57].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>O.C(#N)C.CN(C=O)C>[NH:34]([C:31]1[CH:30]=[CH:29][C:28]([C:27]([O:26][C:24]2[CH:23]=[CH:22][C:21]([CH2:39][CH2:40][C:41](=[O:43])[NH:53][CH2:54][CH2:55][S:56]([OH:59])(=[O:58])=[O:57])=[C:20]([C:17]3[CH2:16][C:15]([CH2:14][C:13]([OH:12])=[O:52])([CH2:44][C:45]([OH:46])=[O:51])[O:19][N:18]=3)[CH:25]=2)=[O:38])=[CH:33][CH:32]=1)[C:35]([NH2:37])=[NH:36]

Participants

8

Reactant 5

HCID 1123TaurineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 178450899HCID 178450899, compound

Product 1

HCID 178512541HCID 178512541, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A mixture of 3-(2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-((4-carbamimidamidobenzoyl)oxy)phenyl)propanoic acid trifluoroacetate (160 mg), taurine (32.5 mg), WSC (50.4 mg), HOBt (43.9 mg), N,N-diisopropylethylamine (0.057 mL), and DMF (5 mL) was stirred overnight at room temperature. The reaction mixture was fractionated by HPLC (C18, mobile phase: water/acetonitrile (system containing 0.1% TFA)). The obtained fraction was concentrated under reduced pressure. To the obtained residue, TFA (4 mL) was added, and the obtained mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and then, the pH of the residue was adjusted to about 4 by the addition of an aqueous ammonium acetate solution. The mixture was stirred at room temperature for 2 hours, and then, the obtained solid was collected by filtration and washed with water and acetone to obtain the title compound (40.3 mg).

Workup

  1. concentrationThe obtained fraction was concentrated under reduced pressure
  2. additionTo the obtained residue, TFA (4 mL) was added
  3. stirringthe obtained mixture was stirred at room temperature for 2 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionthe pH of the residue was adjusted to about 4 by the addition of an aqueous ammonium acetate solution
  6. stirringThe mixture was stirred at room temperature for 2 hours
  7. filtrationthe obtained solid was collected by filtration
  8. washwashed with water and acetone

Sources & evidence

ORD record
ord-bdd19a4f2d3a40a0a815a8773fd0112b
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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