Methanesulfonyl chloride → HCID 86730209, compound

HRID 1850183Notes

Reaction equation

HRID 1850183 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][C:12]2[N:17]=[C:16]([N:18]3[C@@H:22]([CH:23]([CH3:25])[CH3:24])[CH2:21][O:20][C:19]3=[O:26])[CH:15]=[CH:14][N:13]=2)[CH3:10])=[CH:5][CH:4]=1.CS([Cl:31])(=O)=O.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:31][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][C:12]2[N:17]=[C:16]([N:18]3[C@@H:22]([CH:23]([CH3:25])[CH3:24])[CH2:21][O:20][C:19]3=[O:26])[CH:15]=[CH:14][N:13]=2)[CH3:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86730160(S)-3-(2-((S)-1-(4-(hydroxymethyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one

Product 1

HCID 86730209HCID 86730209, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-(2-((S)-1-(4-(hydroxymethyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one (71 mg, 0.2 mmol) in DCM (2 mL) was added methanesulfonyl chloride (27 mg, 0.24 mmol) and DIPEA (0.070 mL, 0.4 mmol). The solution was stirred for 16 h at room temperature then washed with water and brine. After separation, the organic phase was dried over Na2SO4, filtered and concentrated. The crude product was used to next step without further purification.

Workup

  1. washthen washed with water and brine
  2. customAfter separation
  3. dry with materialthe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was used to next step without further purification

Sources & evidence

ORD record
ord-57340cf281884ae0b4b06af89e3b55d4
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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