Methanesulfonyl chloride → HCID 86588707, compound

HRID 887658Notes

Reaction equation

HRID 887658 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][C:13](CO)([C:15]([OH:17])=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([CH2:15][O:17][S:21]([CH3:20])(=[O:23])=[O:22])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68530600HCID 68530600, compound

Product 1

HCID 86588707HCID 86588707, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Hydroxymethyl-azetidine-1,3-dicarboxylic acid monobenzyl ester (6.6 g) was dissolved in CH2Cl2 (100 mL) and brought to −15 C. While stirring, TEA was added (3 eq, 9.43 g) followed by methanesulphonic chloride (2.0 eq, 7.69 g) and allowed to come to RT and stirred for 1 h. The resulting organic solution was extracted with water (3×100 mL). The organic layer was dried over Na2SO4 and evaporated to give the desired product as a clear oil which was used without further purification.

Workup

  1. additionTEA was added (3 eq, 9.43 g)
  2. customto come to RT
  3. stirringstirred for 1 h
  4. extractionThe resulting organic solution was extracted with water (3×100 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-d1b455b0f32e48399ccd55ff766901df
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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