Trifluoroacetic acid → HCID 66722795, compound

HRID 1639534Notes

Reaction equation

HRID 1639534 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[OH:14])[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[NH2:2].[C:15]([N:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].N1CCOCC1.C(O)(C(F)(F)F)=O>CO.ClCCl>[C:18]([O:17][C:15]([N:22]1[CH2:27][CH2:26][C:25]2([NH:2][C:1](=[O:3])[C:4]3[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=[CH:12][C:13]=3[O:14]2)[CH2:24][CH2:23]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8083MorpholineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 10607886Benzoic acid, 3-(aminocarbonyl)-4-hydroxy-, methyl ester

Product 1

HCID 66722795HCID 66722795, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 125 mg (0.64 mmol) of methyl 3-carbamoyl-4-hydroxybenzoate, 192 mg (0.96 mmol) of 1-Boc-4-piperidone, and 120 μL of morpholine in 10 mL of MeOH is refluxed for 72 hr. The MeOH is removed by rotoevapoation, and DCM is added to the residue. Insoluble material is filtered off, and the filtrate is concentrated by rotoevaporation. The residue is purified by preparative TLC to give 93 mg (0.25 mmol, 39% yield) of 1′-(tert-butyloxycarbonyl)-6-methoxycarbonylspiro[1,3-benzoxazine-2,4′-piperidine]-4(3H)-one which on treatment with 40% TFA in dichloromethane gives the TFA salt of 6-methoxycarbonylspiro[1,3-benzoxazine-2,4′-piperidine]-4(3H)-one in quantitative yield.

Workup

  1. temperatureis refluxed for 72 hr
  2. customThe MeOH is removed by rotoevapoation, and DCM
  3. additionis added to the residue
  4. filtrationInsoluble material is filtered off
  5. concentrationthe filtrate is concentrated by rotoevaporation
  6. customThe residue is purified by preparative TLC

Sources & evidence

ORD record
ord-069857009ea74cb1a94fa9db8f392fbb
Source dataset
uspto-grants-2012_02
Patent number
US08110570B2

Reaction notes

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