Ethanol → HCID 178476316, compound

HRID 1190107Notes

Reaction equation

HRID 1190107 reaction equation
[C:1]([O:4][CH2:5][CH:6]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[N:22](COCC[Si](C)(C)C)[CH:23]=[C:24]([C:26]#[N:27])[N:25]=2)=[O:20])=[C:14]([C:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH:37]=2)[CH:13]=1)[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].C(O)C.[C:45]([OH:51])([C:47]([F:50])([F:49])[F:48])=[O:46].CCOCC.CCCCCC>C(Cl)Cl>[F:48][C:47]([F:50])([F:49])[C:45]([OH:51])=[O:46].[C:9]([O:8][CH2:7][CH:6]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[NH:22][CH:23]=[C:24]([C:26]#[N:27])[N:25]=2)=[O:20])=[C:14]([C:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH:37]=2)[CH:13]=1)[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 702EthanolHCID 6422Trifluoroacetic acidHCID 21584099Diethylether hexaneHCID 59771165Acetic acid 3-acetoxy-2-(4-{[4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbonyl]-amino}-3-cyclohex-1-enyl-phenyl)-propyl ester

Product 1

HCID 178476316HCID 178476316, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of acetic acid 3-acetoxy-2-(4-{[4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbonyl]-amino}-3-cyclohex-1-enyl-phenyl)-propyl ester (as prepared in the previous step, 102 mg, 0.175 mmol) in DCM (2 mL) was treated with ethyl alcohol (EtOH) (60 μl) and TFA (0.6 mL) at RT for 2 h and concentrated in vacuo. The reaction mixture was dissolved in DCM (10 mL) and poured into satd aq NaHCO3. The organic layer was separated, dried (Na2SO4) and concentrated. The solid obtained was suspended in 1:1 ether/hexane, sonicated and concentrated in vacuo. The resulting residue was dried in vacuo to obtain the title compound (57 mg, 57%): 1H-NMR (CDCl3; 400 MHz): δ 12.90 (br s, 1H), 9.75 (s, 1H), 8.32 (d, 1H, J=8.4 Hz), 7.78 (s, 1H), 7.24 (dd, 1H, J=8.4, 2.0 Hz), 7.06 (d, 1H, J=2.0 Hz), 5.82 (br s, 1H), 4.38 (m, 4H), 3.35 (m, 1H), 2.23-2.35 (m, 4H), 2.10 (s, 6H), 1.75-1.92 (m, 4H): Mass spectrum, (ESI, m/z): Calcd. for C24H26N4O5, 451.2 (M+H). found 451.0.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe reaction mixture was dissolved in DCM (10 mL)
  3. additionpoured into satd aq NaHCO3
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe solid obtained
  8. customsonicated
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue was dried in vacuo

Sources & evidence

ORD record
ord-81f124875c594074979f9905af66c206
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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