Trifluoroacetic acid → HCID 69082714, compound

HRID 1396246Notes

Reaction equation

HRID 1396246 reaction equation
[CH2:1]([C@H:3]1[O:11][C@H:10]2[C@H:6]([N:7]=[C:8]([N:12]([CH3:14])[CH3:13])[S:9]2)[C@@H:5]([O:15]CC2C=CC(OC)=CC=2)[C@@H:4]1[O:25]CC1C=CC(OC)=CC=1)[CH3:2].C(O)(C(F)(F)F)=O.[NH4+].[OH-]>ClCCl>[CH3:14][N:12]([CH3:13])[C:8]1[S:9][C@H:10]2[O:11][C@H:3]([CH2:1][CH3:2])[C@@H:4]([OH:25])[C@H:5]([OH:15])[C@H:6]2[N:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 69083388HCID 69083388, compound

Product 1

HCID 69082714HCID 69082714, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of above crude product 41 (260 mg, purity 54% 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 42 (Example 6) as a white solid (38 mg). (ES, m/z): [M+H]+ 247.0. 1H NMR (300 MHz, D2O) δ 6.18-6.21 (d, J=6.6 Hz, 1H), 4.09-4.13 (t, J=6.0 Hz, 1H), 3.91-3.94 (t, J=4.8 Hz, 1H), 3.42-3.44 (m, 2H), 2.92 (s, 6H), 1.69-1.77 (m, 1H), 1.40-1.50 (m, 1H), 0.84-0.89 (t, J=7.5 Hz, 3H).

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-f811ee25403c4509b31c5b16a6768ae0
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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