Methanol → HCID 24997352, compound

HRID 1511842Notes

Reaction equation

HRID 1511842 reaction equation
[NH2:1][C@:2]1([C:14]([OH:16])=[O:15])[CH2:6][CH2:5][C@H:4]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=2)[CH2:3]1.S(Cl)(Cl)=O.[CH3:21]O>>[CH3:21][O:15][C:14]([C@@:2]1([NH2:1])[CH2:6][CH2:5][C@H:4]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=2)[CH2:3]1)=[O:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 24997350HCID 24997350, compound

Product 1

HCID 24997352HCID 24997352, compound

Procedure

The (1R,3S)-1-amino-3-(4-bromo-phenyl)-cyclopentanecarboxylic acid (79 g, 0.28 mol) suspended in MeOH (1.8 L) was cooled in an ice/water bath and thionyl chloride (178 mL, 2.44 mol) was added dropwise. Following the addition the reaction was heated to reflux, resulting in a nearly homogeneous solution. After refluxing for about 36 hours, the reaction mixture was cooled to room temperature, filtered, and rinsed with MeOH (2×200 mL). The filtrate was concentrated in vacuo to provide a white solid. The white solid was triturated with EtOAc (1 L), collected by filtration, rinsed with EtOAc (2×500 mL), and dried under vacuum to give the (1R,3S)-1-amino-3-(4-bromo-phenyl)-cyclopentanecarboxylic acid methyl ester; hydrochloride as a white solid (79 g, 96%).

Workup

  1. temperaturewas cooled in an ice/water bath
  2. additionthe addition the reaction
  3. temperaturewas heated
  4. temperatureto reflux
  5. customresulting in a nearly homogeneous solution
  6. temperatureAfter refluxing for about 36 hours
  7. filtrationfiltered
  8. washrinsed with MeOH (2×200 mL)
  9. concentrationThe filtrate was concentrated in vacuo
  10. customto provide a white solid
  11. customThe white solid was triturated with EtOAc (1 L)
  12. filtrationcollected by filtration
  13. washrinsed with EtOAc (2×500 mL)
  14. customdried under vacuum

Sources & evidence

ORD record
ord-4012d882d603491a941f7e5736ef9a47
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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