Dimethyl Sulfoxide → HCID 68999260, compound

HRID 906648Notes

Reaction equation

HRID 906648 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:35]=[CH:34][C:15]([C:16]([NH:18][CH2:19][C:20]2[S:21][C:22]([S:25]([N:28]3[CH2:32][CH2:31][C@@H:30]([OH:33])[CH2:29]3)(=[O:27])=[O:26])=[CH:23][CH:24]=2)=[O:17])=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([NH:18][CH2:19][C:20]2[S:21][C:22]([S:25]([N:28]3[CH2:32][CH2:31][C:30](=[O:33])[CH2:29]3)(=[O:26])=[O:27])=[CH:23][CH:24]=2)=[O:17])=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 70167641HCID 70167641, compound

Product 1

HCID 68999260HCID 68999260, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At −80° C. oxalylchloride (36 mg, 0.28 mmol) was dissolved in dry CH2Cl2, while DMSO (50 ul, 0.6 mmol) were added slowly. The solution was stirred under Ar. For 15′. 351a (100 mg, 0.25 mmol) was dissolved in 2 ml CH2Cl2, and this solution was added dropwise to the above reaction mixture at −80° C. The reaction was stirred for 15′ at low temperature, before DIEA (0.21 ml, 1.25 mmol) was added. The reaction was stirred at −80° C. for 30′ and allowed to warm to it during 2 h. A white solid was formed, the reaction was quenched with water and extracted with CH2Cl2 several times. The combined organic layers were dried over MgSO4 and evaporated to dryness. The crude was purified by flash chromatography on silica gel using EtOAc/cyclohexane 2:1 as eluent. 351b (80 mg, 80%) was obtained as a colourless solid.: H′ NMR (CDCl3) δ 7.72 (d, J=8.7 Hz, 2H), 7.46 (d, J=3.8 Hz, 1H), 7.42 (d, J=8.7 Hz, 2H), 7.08 (d, J=3.8 Hz, 1H), 6.59 (t, J=5.8, 1H), 4.80 (d, J=6.0 Hz, 2H), 3.58 (t, J=7.5 Hz, 2H), 3.50 (s, 3H), 2.54 (t, J=7.5, 2H), 3.35-3.23 (m, 3H), 2.95 (m, 2H), 1.94 (m, 2H), 1.86 (m, 2H), 1.70-1.50 (m, 5H), 130-1.20 (m, 8H), 0.87 (t, J=6.8, 3H), M/Z APCI-399.0 (M+1), 397.2 (M−1)

Workup

  1. additionwere added slowly
  2. additionthis solution was added dropwise to the above reaction mixture at −80° C
  3. stirringThe reaction was stirred for 15′ at low temperature
  4. stirringThe reaction was stirred at −80° C. for 30′ and
  5. temperatureto warm to it during 2 h
  6. customA white solid was formed
  7. customthe reaction was quenched with water
  8. extractionextracted with CH2Cl2 several times
  9. dry with materialThe combined organic layers were dried over MgSO4
  10. customevaporated to dryness
  11. customThe crude was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-fcbd95d223754299af10f9ee30c6f670
Source dataset
uspto-grants-2011_09
Patent number
US08012995B1

Reaction notes

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