Hydrochloric Acid → HCID 59558758, compound

HRID 2388762Notes

Reaction equation

HRID 2388762 reaction equation
C(OC(=O)[C@H](OC1C=C(Cl)N=C(SCC2C=CC=C(F)C=2F)N=1)C)C.C([O:28][C:29](=[O:57])[C@H:30]([O:32][C:33]1[CH:38]=[C:37]([NH:39][S:40]([N:43]2[CH2:46][CH2:45][CH2:44]2)(=[O:42])=[O:41])[N:36]=[C:35]([S:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([F:55])[C:50]=2[F:56])[N:34]=1)[CH3:31])C.[OH-].[Na+].Cl>CO>[N:43]1([S:40]([NH:39][C:37]2[N:36]=[C:35]([S:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[C:51]([F:55])[C:50]=3[F:56])[N:34]=[C:33]([O:32][C@H:30]([CH3:31])[C:29]([OH:57])=[O:28])[CH:38]=2)(=[O:42])=[O:41])[CH2:46][CH2:45][CH2:44]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59558764HCID 59558764, compoundHCID 866198702-[[6-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy](2R)-propanoic acid ethyl ester

Product 1

HCID 59558758HCID 59558758, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[[6-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy]-(2R)-propanoic acid ethyl ester (the product of example 23) (0.24 g) in methanol (1 mL) was added 1M aqueous sodium hydroxide (1 mL). The resulting mixture was stirred at ambient temperature for 16 h. The reaction mixture was acidified using 2 M aqueous HCl, then extracted with EtOAc (×2). The combined organics were washed with brine then dried (MgSO4), filtered and evaporated. The resulting oil was triturated with DCM/iso-hexane to give the title compound was a white solid. Yield: 0.20 g

Workup

  1. extractionextracted with EtOAc (×2)
  2. washThe combined organics were washed with brine
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting oil was triturated with DCM/iso-hexane

Sources & evidence

ORD record
ord-d6ef9c318eef45178773ae3e54b30daa
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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