Ammonium Acetate → HCID 178525168, compound

HRID 1027140Notes

Reaction equation

HRID 1027140 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:15]2([CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[O:14][CH2:13][C@H:12]1[C:21](=O)[NH:22][CH2:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][CH:27]=1)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:38]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[C:15]2([CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[O:14][CH2:13][C@H:12]1[C:21]1[NH:22][CH:23]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][CH:27]=2)[N:38]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 67386734HCID 67386734, compound

Product 1

HCID 178525168HCID 178525168, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

(S)-3-[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-1,8-dioxa-4-aza-spiro[4.5]decane-4-carboxylic acid benzyl ester (1.13 gm, 2.18 mmol) was dissolved in xylenes (11 mL), ammonium acetate (0.84 gm, 10.94 mmol) was added as a solid and the mixture was heated at 140° C. for 24 h. The mixture was diluted with ethyl acetate (50 mL) and the organic layer was washed (aqueous NaHCO3, water, brine) and dried. This crude product was purified by silica gel chromatography (3:2 mixture of EtOAc:hexanes) to afford 0.62 gm (57%) of the title compound. LCMS 500.9 (M+2)

Workup

  1. washthe organic layer was washed (aqueous NaHCO3, water, brine)
  2. customdried
  3. customThis crude product was purified by silica gel chromatography (3:2 mixture of EtOAc:hexanes)

Sources & evidence

ORD record
ord-0fb3ef21b38347f98068733f334c2fd2
Source dataset
uspto-grants-2014_05
Patent number
US08729077B2

Reaction notes

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