Formic Acid → HCID 90408859, compound

HRID 1855078Notes

Reaction equation

HRID 1855078 reaction equation
[F:1][C:2]([F:33])([F:32])[S:3]([O:6][C:7]1[CH:8]=[C:9]([C:13]23[CH2:20][CH2:19][C:16]([CH2:21][CH2:22][O:23][CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])([CH2:17][CH2:18]2)[CH2:15][O:14]3)[CH:10]=[CH:11][CH:12]=1)(=[O:5])=[O:4].C(O)=O>C(Cl)Cl>[F:33][C:2]([F:1])([F:32])[S:3]([O:6][C:7]1[CH:8]=[C:9]([C:13]23[CH2:18][CH2:17][C:16]([CH2:21][CH2:22][O:23][CH2:24][C:25]([OH:27])=[O:26])([CH2:19][CH2:20]2)[CH2:15][O:14]3)[CH:10]=[CH:11][CH:12]=1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 90409180HCID 90409180, compound

Product 1

HCID 90408859HCID 90408859, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2-(2-(1-(3-(((trifluoromethyl)sulfonyl)oxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate (28 mg, 0.057 mmol) and formic acid (0.022 mL, 0.57 mmol) in CH2Cl2 (0.5 mL) was stirred at rt for 18 h, then was concentrated in vacuo. The crude material was purified by preparative LC/MS (Column: Waters XBridge C18, 19×100 mm, 5-nm particles; Mobile Phase A: 5:95 MeCN:water with 0.1% TFA; Mobile Phase B: 95:5 MeCN:water with 0.1% TFA; Gradient: 40-80% B over 10 min, then a 5-min hold at 100% B; Flow rate: 20 mL/min) to give the title compound (19 mg, 0.043 mmol, 76% yield) as a clear oil. LCMS [M−H]+=437.0; 1H NMR (DMSO-d6) δ: 7.53-7.48 (m, 2H), 7.42 (d, J=2.7 Hz, 1H), 7.34 (dt, J=7.3, 2.3 Hz, 1H), 3.96 (s, 2H), 3.80 (s, 2H), 3.50 (t, J=6.7 Hz, 2H), 2.16-2.05 (m, 2H), 1.89-1.74 (m, 2H), 1.73-1.59 (m, 4H), 1.42 (t, J=6.8 Hz, 2H).

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe crude material was purified by preparative LC/MS (Column
  3. waitGradient: 40-80% B over 10 min
  4. customa 5-min hold

Sources & evidence

ORD record
ord-ce089066d4d3451ea063c77b2dbafd65
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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