Taurine → HCID 86669793, compound

HRID 2371300Notes

Reaction equation

HRID 2371300 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([C:22]2[CH:26]=[C:25]([C:27]3[CH:28]=[C:29]([C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=4)[CH:30]=[CH:31][CH:32]=3)[O:24][N:23]=2)[CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:61][CH2:62][CH2:63][S:64]([OH:67])(=[O:66])=[O:65]>CN(C=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C@@H:11]([C:22]2[CH:26]=[C:25]([C:27]3[CH:28]=[C:29]([C:33]4[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=4)[CH:30]=[CH:31][CH:32]=3)[O:24][N:23]=2)[CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([NH:61][CH2:62][CH2:63][S:64]([OH:67])(=[O:66])=[O:65])=[O:18])=[CH:20][CH:21]=2)=[CH:9][CH:10]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 1123TaurineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 67490623HCID 67490623, compound

Product 1

HCID 86669793HCID 86669793, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (S)-4-{2-(4-tert-Butyl-phenyl)-2-[5-(4′-chloro-biphenyl-3-yl)-isoxazol-3-yl]-ethyl}-benzoic acid (0.25 g, 0.46 mmol), EDCI (133 mg, 0.69 mmol), HOBt (107 mg, 0.69 mmol), N,N-diispropylethylamine (0.25 mL, 1.95 mmol) in DMF (10 mL), and followed by taurine (116 mg, 0.093 mmol) was added. The resulting mixture was stirred for 14 h and monitored by LCMS after completion of the reaction the solvent was removed under reduced pressure. The resulting mixture was purified by column chromatography on C-18, eluting with H2O/Acetonitrile 40% to afford (4-{2-(4-tert-Butyl-phenyl)-2-[5-(4′-chloro-biphenyl-3-yl)-isoxazol-3-yl]-ethyl}-benzoylamino)ethane sulfonic acid (29) as a white solid. (125 mg, 42%): 1H NMR (300 MHz, MeOD): 8.01 (s, 1H), 7.78 (d, J=6.9 Hz, 2H), 7.70-7.47 (m, 6H), 7.35 (d, J=9.0 Hz, 2H), 7.30 (d, J=8.1 Hz, 2H), 6.86 (s, 1H), 4.47 (t, J=6.9 Hz, 1H), 3.85-3.70 (m, 2H), 3.75 (dd, J=4.9, 13.2 Hz, 1H), 3.25-3.05 (m, 2H), 1.31 (s, 9H); LC-MS m/z=643 [C36H35ClN2O5S]+; HPLC conditions: Waters Atlantis C-18 OBD 4.6×150 mm; mobile phase=ACN/(H2O:0.1 TFA) flow rate=1.0 mL/min; detection=UV @ 254 and 220 nm retention time in min: 21.20; Anal Calcd: (MF:C36H35ClN2O5S+1.5H2O+0.2 CH2Cl2) Calcd: C, 63.27; H, 5.63; N, 4.08. Found: C, 63.24; H, 5.75; N, 3.96. αD[25] MeOH (4.66 mg in 1.0 mL)=+13.487.

Workup

  1. additionwas added
  2. customafter completion of the reaction the solvent
  3. customwas removed under reduced pressure
  4. customThe resulting mixture was purified by column chromatography on C-18
  5. washeluting with H2O/Acetonitrile 40%

Sources & evidence

ORD record
ord-7c49ef9551554cb1af4fe801ae56e975
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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