Methanol → HCID 58118684, compound

HRID 1615836Notes

Reaction equation

HRID 1615836 reaction equation
C(OC([N:8]1[CH2:17][C@:16]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)([CH3:18])[N:15]([CH2:27][C:28]([OH:30])=[O:29])[C:14](=[O:31])[C:9]21[CH2:13][CH2:12][CH2:11][CH2:10]2)=O)(C)(C)C.OS(O)(=O)=O.[CH3:37]O>>[F:25][C:23]1[CH:24]=[C:19]([C@@:16]2([CH3:18])[N:15]([CH2:27][C:28]([O:30][CH3:37])=[O:29])[C:14](=[O:31])[C:9]3([CH2:10][CH2:11][CH2:12][CH2:13]3)[NH:8][CH2:17]2)[CH:20]=[C:21]([F:26])[CH:22]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 58118680HCID 58118680, compound2×

Product 1

HCID 58118684HCID 58118684, compound

Procedure

A mixture of [(8R)-6-(tert-butoxycarbonyl)-8-(3,5-difluorophenyl)-8-methyl-10-oxo-6,9-diazaspiro[4.5]dec-9-yl]acetic acid (4.41 g, 10.1 mmol, described in Intermediate 21) and conc. H2SO4 (3.0 mL) in MeOH (100 mL) was heated at reflux for 24 h. The reaction mixture was concentrated in vacuo to a volume of about 30 mL, poured into saturated aqueous NaHCO3 (150 mL), and extracted with EtOAc (2×200 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound. MS: m/z=353 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. concentrationThe reaction mixture was concentrated in vacuo to a volume of about 30 mL
  4. additionpoured into saturated aqueous NaHCO3 (150 mL)
  5. extractionextracted with EtOAc (2×200 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e33e209d8704aa4a61a79bc883ade93
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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