Trifluoroacetic acid → HCID 69083309, compound

HRID 1396247Notes

Reaction equation

HRID 1396247 reaction equation
COC1C=CC(C[O:8][C@@H:9]2[C@@H:17]([CH:18]=[CH2:19])[O:16][C@H:15]3[C@H:11]([N:12]=[C:13]([N:20]([CH3:22])[CH3:21])[S:14]3)[C@H:10]2[O:23]CC2C=CC(OC)=CC=2)=CC=1.C(O)(C(F)(F)F)=O.[NH4+].[OH-]>ClCCl>[CH3:22][N:20]([CH3:21])[C:13]1[S:14][C@H:15]2[O:16][C@H:17]([CH:18]=[CH2:19])[C@@H:9]([OH:8])[C@H:10]([OH:23])[C@H:11]2[N:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 69083952HCID 69083952, compound

Product 1

HCID 69083309HCID 69083309, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of above crude product 40 (220 mg, purity 57% by LC-MS) in dichloromethane (10 mL) was treated with TFA (1 mL) for 4 hours at room temperature. The solution was adjusted to pH at 8 with NH4OH, and then condensed to give a crude product, which was purified by Prep-HPLC with the following conditions (Agilent 1200 prep HPLC: Column, SunFire Prep C18, 19*50 mm 5 um; mobile phase, WATER with 0.03% NH4OH and CH3CN (10% CH3CN up to 45% in 10 min; Detector, UV 220 nm) to provide compound 43 (Example 7) as a white solid (35.7 mg). (ES, m/z): 245.0. 1H NMR (300 MHz, D2O) δ 6.20-6.22 (d, J=6.3 Hz, 1H), 5.79-5.87 (m, 1H), 5.30-5.38 (m, 2H), 3.98-4.08 (m, 2H), 3.87-3.91 (t, J=6.0 Hz, 1H), 3.46-3.52 (m, 1H), 2.93 (s, 6H).

Workup

  1. customcondensed
  2. customto give a crude product, which
  3. customwas purified by Prep-HPLC with the following conditions (Agilent 1200 prep HPLC

Sources & evidence

ORD record
ord-b3122368043f42ee863a3aef879a1db6
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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