3-Hydroxybenzoic Acid → HCID 18536664, compound

HRID 412049Notes

Reaction equation

HRID 412049 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[C:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].CC[N:26](CC)CC.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>C(Cl)Cl.C(Cl)Cl.CO>[C:14]([O:13][C:11]([N:18]1[CH2:19][CH2:20][N:21]([C:3]2[C:2]([OH:1])=[CH:10][CH:9]=[CH:8][C:4]=2[C:5]([NH2:26])=[O:7])[CH2:22][CH2:23]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 74203-Hydroxybenzoic AcidHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chloride

Product 1

HCID 18536664HCID 18536664, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

3-Hydroxybenzoic acid (0.483 g, 3.5 mmol), BOC piperazine (0.737 g, 3.96 mmol), Et3N (0.92 mL, 6.66 mmol), and CH2Cl2 (10 mL) were combined, cooled to 4° and solid Bis(2-oxo-3-oxazolidinyl)-phosphinic chloride (0.889 g, 3.5 mmol) was added under Ar. The ice bath was removed and a clear solution was obtained on warming to 23°. After 1 h tlc (silica plates, 19:1 CH2Cl2/CH3OH) indicated a completed reaction. The reaction was diluted with CH2Cl2 (100 mL), washed with 0.3 N HCl (20 mL), H2O (20 mL), satd aq NaHCO3 (20 mL) and satd aq NaCl (20 mL), dried (Na2SO4) filtered and concentrated to afford the title compound as a white foam. 1H NMR (CDCl3): d 7.20 (m, 1), 6.90 (s, 1), 6.86 (d, 1), 6.82 (d, 1), 3.69 (m, 2), 3.59 (m,2), 3.39 (m, 4), 1.46 (s, 9),

Workup

  1. temperaturecooled to 4°
  2. customThe ice bath was removed
  3. customa clear solution was obtained
  4. temperatureon warming to 23°
  5. customa completed reaction
  6. washwashed with 0.3 N HCl (20 mL), H2O (20 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5a6cff35ef9440cea3574e74a5048d9f
Source dataset
uspto-grants-2003_05
Patent number
US06562832B1

Reaction notes

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