Trifluoroacetic acid → HCID 178451563, compound

HRID 1639538Notes

Reaction equation

HRID 1639538 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[NH:15][N:14]=[N:13][N:12]=2)=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:16]([N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].N1CCOCC1.C(O)(C(F)(F)F)=O>CO.ClCCl>[C:19]([O:18][C:16]([N:23]1[CH2:28][CH2:27][C:26]2([NH:6][C:4](=[O:5])[C:3]3[CH:7]=[C:8]([C:11]4[NH:15][N:14]=[N:13][N:12]=4)[CH:9]=[CH:10][C:2]=3[O:1]2)[CH2:25][CH2:24]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8083MorpholineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178513596HCID 178513596, compound

Product 1

HCID 178451563HCID 178451563, compoundYield 21.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 75 mg (0.37 mmol) of 2-hydroxy-5-(1H-tetrazol-5-yl)benzamide, 110 mg (0.55 mmol) of 1-Boc-4-piperidone, and 71 μL of morpholine in 8 mL of MeOH is refluxed for 72 hr. The MeOH is removed by rotoevapoation and the residue is purified by preparative TLC to give 29 mg (0.08 mmol, 15% yield) of 1′-(tert-butyloxycarbonyl)-6-(1H-tetrazol-5-yl)spiro[1,3-benzoxazine-2,4′-piperidine]-4(3H)-one which on treatment with 40% TFA in dichloromethane at room temperature for 3 hr. gives the TFA salt of 6-(1H-tetrazol-5-yl)spiro[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
  3. customthe residue is purified by preparative TLC

Sources & evidence

ORD record
ord-77b9f0875b21484a8e01ba4ba82811f9
Source dataset
uspto-grants-2012_02
Patent number
US08110570B2

Reaction notes

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