Diisopropylamine → HCID 58149217, compound

HRID 1920018Notes

Reaction equation

HRID 1920018 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:6]=1[OH:15])[CH3:2].C(NC(C)C)(C)C.Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C(Cl)Cl>[CH2:27]([O:26][C:24](=[O:25])[N:3]([CH2:1][CH3:2])[CH2:4][C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:6]=1[OH:15])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 10387Benzyl chloroformate2×HCID 57419866HCID 57419866, compound

Product 1

HCID 58149217HCID 58149217, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-ethylaminomethyl-4-methanesulfonyl-phenol (0.229 g, 1.0 mmol) and diisopropylamine (0.94 mL, 2.5 mmol) in CH2Cl2 (10 mL) was added benzyl chloroformate (0.16 mL, 1.1 mmol). Some over-acylation product was observed, so additional benzyl chloroformate (0.21 mL) was added to convert all of the product to the diacylated product. After aqueous work-up, the organic layer was concentrated, and the residue was dissolved in MeOH (10 mL) and treated with 1N aqueous LiOH (4 mL). Once the hydrolysis was complete, the mixture was worked-up, and the residue was purified to give the title compound.

Workup

  1. concentrationAfter aqueous work-up, the organic layer was concentrated
  2. dissolutionthe residue was dissolved in MeOH (10 mL)
  3. additiontreated with 1N aqueous LiOH (4 mL)
  4. customthe residue was purified

Sources & evidence

ORD record
ord-eb87cc9d527d429da6c3b93e6dc953d2
Source dataset
uspto-grants-2012_05
Patent number
US08168678B2

Reaction notes

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