Diisopropylethylamine → (s)-2-(3-Adamantan-2-yl-ureido)-3,3-dimethyl-butyric acid methyl ester

HRID 1092305Notes

Reaction equation

HRID 1092305 reaction equation
[CH3:1][C:2]([CH:5]([NH2:10])[C:6]([O:8][CH3:9])=[O:7])([CH3:4])[CH3:3].C(N(C(C)C)C(C)C)C.[CH:20]12[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH:21]1[N:30]=[C:31]=[O:32])[CH2:27]2>CN(C=O)C>[CH3:9][O:8][C:6](=[O:7])[C@@H:5]([NH:10][C:31]([NH:30][CH:21]1[CH:20]2[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]1[CH2:23]3)[CH2:27]2)=[O:32])[C:2]([CH3:4])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3831185Methyl DL-tert-leucinateHCID 128826302-Isocyanatoadamantane

Product 1

HCID 57495618(s)-2-(3-Adamantan-2-yl-ureido)-3,3-dimethyl-butyric acid methyl esterYield 91.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-(+)-Methyl-tert-leucinate hydrochloride (564 mg) was dissolved in abs. DMF and then N-ethyl-diisopropylamine (0.68 mL) was added drop by drop. The mixture was allowed to stir for 30 minutes at RT and then 2-adamantyl isocyanate (500 mg) was added in one portion. Stirring was continued over night at RT. The reaction mixture was evaporated to dryness and residual DMF was removed by co-evaporation with toluene. The residue was purified by flash chromatography using 5% methanol in DCM as an eluent to give (S)-2-(3-adamantan-2-yl-ureido)-3,3-dimethyl-butyric acid methyl ester (834 mg) as a white solid. MS (EI): 322.4 (M+).

Workup

  1. stirringStirring
  2. waitwas continued over night at RT
  3. customThe reaction mixture was evaporated to dryness and residual DMF
  4. customwas removed by co-evaporation with toluene
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-db6f1d47b881485b89655fe66ce4794d
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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