Lithium borohydride → N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1S)-2-hydroxy-1-methylethoxy]-4-pyrimidinyl]-1-azetidinesulfonamide

HRID 2388758Notes

Reaction equation

HRID 2388758 reaction equation
[N:1]1([S:5]([NH:8][C:9]2[N:14]=[C:13]([S:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=3[F:24])[N:12]=[C:11]([O:25][C@@H:26]([CH3:32])[C:27](OCC)=[O:28])[CH:10]=2)(=[O:7])=[O:6])[CH2:4][CH2:3][CH2:2]1.[BH4-].[Li+]>C1COCC1>[F:24][C:18]1[C:19]([F:23])=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][S:15][C:13]1[N:14]=[C:9]([NH:8][S:5]([N:1]2[CH2:4][CH2:3][CH2:2]2)(=[O:6])=[O:7])[CH:10]=[C:11]([O:25][C@@H:26]([CH3:32])[CH2:27][OH:28])[N:12]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 670512112-[[6-[(1-azetidinylsulfonyl)amino]-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy]-(2S)-propanoic acid ethyl ester

Product 1

HCID 59558803N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1S)-2-hydroxy-1-methylethoxy]-4-pyrimidinyl]-1-azetidinesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound was prepared according to the procedure outlined in example 24 using 2-[[6-[(1-azetidinylsulfonyl)amino]-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy]-(2S)-propanoic acid, ethyl ester, (the product of step (0.28 g), THF (8 mL) and 2 M lithium borohydride in THF (0.57 mL). Purification was by column chromatography on silica using EtOAc/isohexane (2:3) as eluent to give the title compound as a white solid. Yield: 0.15 g

Workup

  1. customThe title compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-1c50f250848547a4b0095d1c4f3e96d3
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

Loading…