Water → HCID 59393687, compound

HRID 2092133Notes

Reaction equation

HRID 2092133 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([C:25]3[N:30]=[CH:29][C:28]([C:31]4[N:35]=[C:34]([CH2:36][OH:37])[O:33][N:32]=4)=[CH:27][CH:26]=3)([CH3:24])[CH:21]([CH3:23])[CH3:22])=[CH:16][CH:15]=2)[CH:11]=[N:12][CH:13]=1.C(N(CC)C(C)C)(C)C.O>C(Cl)Cl>[CH3:1][S:2]([O:37][CH2:36][C:34]1[O:33][N:32]=[C:31]([C:28]2[CH:29]=[N:30][C:25]([C:20]([C:17]3[CH:18]=[CH:19][C:14]([C:10]4[CH:11]=[N:12][CH:13]=[C:8]([O:7][CH3:6])[CH:9]=4)=[CH:15][CH:16]=3)([CH3:24])[CH:21]([CH3:22])[CH3:23])=[CH:26][CH:27]=2)[N:35]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59393706HCID 59393706, compound

Product 1

HCID 59393687HCID 59393687, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (28.0 μL, 0.362 mmol) was added to a stirred solution of 1d (104 mg, 0.241 mmol) and N,N-diisopropylethylamine (105 μL, 0.602 mmol) in DCM (2.00 mL) at 0° C. After approximately 20 min, the reaction mixture was poured into water and extracted three times with EtOAc. The combined organic extracts were washed with water and brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound 1e, which was used without further purification.

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad40d4f4002443bf928be0d409d428dc
Source dataset
uspto-grants-2013_05
Patent number
US08440672B2

Reaction notes

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