Methanesulfonyl chloride → HCID 131729159, compound

HRID 905977Notes

Reaction equation

HRID 905977 reaction equation
CCN(C(C)C)C(C)C.[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[Cl:20])[CH:16]([OH:21])[N:15]([CH:22]1[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23]1)[CH:14]2[OH:28].[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[Cl:20])[CH:16]([OH:21])[N:15]([C@@H:22]1[CH2:26][CH2:25][C@H:24]([O:27][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:23]1)[CH:14]2[OH:28]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67386033HCID 67386033, compound

Product 1

HCID 131729159HCID 131729159, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask was added DCM (40 mL), DIPEA (2.0 mL, 11.48 mmol), c is 5,6-dichloro-2-(3-hydroxy-cyclopentyl)-2,3-dihydro-1H-isoindole-1,3-diol 1.071 g, 3.57 mmol) and methanesulfonyl chloride (0.6 mL, 7.72 mmol) and the mixture stirred overnight at RT. The mixture was concentrated in vacuo, EtOAc (100 mL) and H2O (100 mL) added, filtered off insolubles, separated and extracted the aqueous layer with EtOAc (50 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo to give cis methanesulfonic acid 3-(5,6-dichloro-1,3-dihydroxy-1,3-dihydro-isoindol-2-yl)-cyclopentyl ester as a tan solid (1.5 g, impure as >100% yield).

Workup

  1. concentrationThe mixture was concentrated in vacuo, EtOAc (100 mL) and H2O (100 mL)
  2. additionadded
  3. filtrationfiltered off insolubles
  4. customseparated
  5. extractionextracted the aqueous layer with EtOAc (50 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44170551ad1845978fd1774296563d3a
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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