Hydrochloric Acid → HCID 54691692, compound

HRID 1034219Notes

Reaction equation

HRID 1034219 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[C:18](OC(C)(C)C)(=[O:26])[C:19](OC(C)(C)C)=[O:20].CC(C)([O-])C.[K+].Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:19](=[O:20])[C:18]([OH:26])=[C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69651Di-tert-butyl oxalateHCID 19023587HCID 19023587, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54691692HCID 54691692, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the title compound of Example C (5.41 g, 22.6 mmol) in dry THF (100 ml) was added di-tert-butyl oxalate (4.57 g, 22.6 mmol), followed by potassium tert-butoxide (5.07 g, 45.2 mmol) and the resulting dark yellow solution was stirred for 84 h at room temperature. The reaction mixture was then acidified with 1N HCl to pH=3, followed by the addition of H2O (35 ml) and the mixture was then extracted with CH2Cl2. The combined organic layers were dried with MgSO4, filtered and dried to give a solid which was chromatographed on silica gel eluting with 1/1/98 MeOH/HOAc/CH2Cl2 to give the title compound (3.166 g, 48%). Anal calcd for C15H16NO4F: C, 61.43; H, 5.50; N, 4.78. Found: C, 61.16; H, 5.50; N, 4.77.

Workup

  1. extractionthe mixture was then extracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried with MgSO4
  3. filtrationfiltered
  4. customdried
  5. customto give a solid which
  6. customwas chromatographed on silica gel eluting with 1/1/98 MeOH/HOAc/CH2Cl2

Sources & evidence

ORD record
ord-3a02d97c908344fab68f2e88032b099e
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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