Dicyclohexylcarbodiimide → Ethyl 2,2-dimethyl-3-[(methylsulfonyl)amino]-3-oxopropanoate

HRID 1992063Notes

Reaction equation

HRID 1992063 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[C:5]([CH3:10])([CH3:9])[C:6](O)=[O:7])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1.CN(C1C=CC=CN=1)C.[CH3:36][S:37]([NH2:40])(=[O:39])=[O:38]>C(Cl)Cl>[CH3:9][C:5]([CH3:10])([C:6]([NH:40][S:37]([CH3:36])(=[O:39])=[O:38])=[O:7])[C:4]([O:3][CH2:1][CH3:2])=[O:11]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 72879MethanesulfonamideHCID 2317543-Ethoxy-2,2-dimethyl-3-oxopropanoic acid

Product 1

HCID 58728441Ethyl 2,2-dimethyl-3-[(methylsulfonyl)amino]-3-oxopropanoateYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Ethoxy-2,2-dimethyl-3-oxopropanoic acid (100 mg, 0.624 mmole) was added to a stirring suspension of 2.5 equivalents of PS-DCC from Argonaut and 3 equivalents of dimethylaminopyridine in DCM. To this was added methanesulfonamide (41.6 mg, 0.437 mmole). The solution was filtered of and concentrated to give 69.3 mg of ethyl 2,2-dimethyl-3-[(methylsulfonyl)amino]-3-oxopropanoate (67% yield crude). MS ES− 236 (M−H). 1H NMR (300 MHz, Chloroform-d) δ ppm 1.4 (t, J=6.7 Hz, 3H), 1.6 (s, 6H), 3.3 (m, 3H), 4.3 (m, 2H).

Workup

  1. filtrationThe solution was filtered of and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-3747be02fe8f43b9a6c5a833706ba13f
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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