Chloromethyl pivalate → HCID 12918077, compound

HRID 1979924Notes

Reaction equation

HRID 1979924 reaction equation
[C:1]([S:9][CH2:10][C@@H:11]([CH3:22])[C:12]([N:14]1[C@H:18]([C:19]([OH:21])=[O:20])[CH2:17][S:16][CH2:15]1)=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:29][CH2:30]Cl)(=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25]>CN(C)C=O.C(N(CC)CC)C>[C:1]([S:9][CH2:10][C@@H:11]([CH3:22])[C:12]([N:14]1[C@H:18]([C:19]([O:21][CH2:30][O:29][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[O:20])[CH2:17][S:16][CH2:15]1)=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 87885Chloromethyl pivalateHCID 12915526HCID 12915526, compound

Product 1

HCID 12918077HCID 12918077, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

Under a nitrogen atmosphere, to the solution of 3.4 g of (4R)-3-[(2S)-S-benzoyl-3-mercapto-2-methylpropanoyl]-4-thiazolidinecarboxylic acid in 11 ml of dry N,N-dimethylformamide, 1.4 ml of triethylamine and 1.5 g of chloromethyl pivalate are added, and stirred at 90° C. for 6 hours. The reaction mixture is poured into 100 ml of ice-water, and extracted with ether. The organic layer is washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo to give oil, yield 4.8 g. The oil is purified by silica gel column chromatography to give the titled compound, yield 4.1 g (91%), mp. 69°-69.5° C. (benzene-n-hexane), [α]D25 -153.8° (c=1.0, methanol).

Workup

  1. extractionextracted with ether
  2. washThe organic layer is washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give oil, yield 4.8 g
  6. customThe oil is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a05670a81b2a4aa9b445b250d7ad0527
Source dataset
uspto-grants-1984_11
Patent number
US04483861

Reaction notes

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