Lithium borohydride → HCID 11496028, compound

HRID 1024870Notes

Reaction equation

HRID 1024870 reaction equation
C([O:3][C:4](=O)[C@H:5]([O:7][C:8]1[CH:13]=[C:12]([NH:14][S:15]([N:18]2[CH2:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])[N:11]=[C:10]([S:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=2[F:31])[N:9]=1)[CH3:6])C.[BH4-].[Li+]>C1COCC1>[F:31][C:25]1[C:26]([F:30])=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][S:22][C:10]1[N:11]=[C:12]([NH:14][S:15]([N:18]2[CH2:21][CH2:20][CH2:19]2)(=[O:16])=[O:17])[CH:13]=[C:8]([O:7][C@H:5]([CH3:6])[CH2:4][OH:3])[N:9]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 59558764HCID 59558764, compound

Product 1

HCID 11496028HCID 11496028, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2-[[6-[(1-azetidinylsulfonyl)amino]-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy]-(2R)-propanoic acid ethyl ester, (the product of example 23) (0.40 g) in THF (10 mL) was added 2M lithium borohydride in THF (0.82 mL) dropwise and the mixture was stirred at ambient temperature for 20 h. The reaction mixture was cooled to 0° C. and quenched with 1M aqueous hydrochloric acid. The resulting mixture was extracted with EtOAc (×2). The combined organic layers were washed with 1M aqueous hydrochloric acid then brine and was dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography on silica gel using EtOAc/isohexane (1:1) as eluent. The resulting oil was triturated with DCM to give the title compound as a white solid. Yield: 0.25 g

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched with 1M aqueous hydrochloric acid
  3. extractionThe resulting mixture was extracted with EtOAc (×2)
  4. washThe combined organic layers were washed with 1M aqueous hydrochloric acid
  5. dry with materialbrine and was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel
  9. customThe resulting oil was triturated with DCM

Sources & evidence

ORD record
ord-4eecc499418c4acaab0956cee9360e30
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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