Potassium Carbonate → HCID 86758000, compound

HRID 843751Notes

Reaction equation

HRID 843751 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:29])[CH2:6][C@@H:7]([C:27]#[CH:28])[NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17](=[O:26])[CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH2:12]1)=[O:10])[CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:37][C:38]1[O:39][C:40](=[O:44])[O:41][C:42]=1[CH3:43].[Cl-].[NH4+]>CN(C)C=O>[CH2:2]([O:4][C:5](=[O:29])[CH2:6][C@@H:7]([C:27]#[CH:28])[NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17](=[O:26])[CH2:18][CH2:19][CH:20]2[CH2:21][CH2:22][N:23]([CH2:37][C:38]3[O:39][C:40](=[O:44])[O:41][C:42]=3[CH3:43])[CH2:24][CH2:25]2)[CH2:12]1)=[O:10])[CH3:3]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-oneHCID 86758001HCID 86758001, compound

Product 1

HCID 86758000HCID 86758000, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of N-[(R)-1-{3-(4-piperidyl)propionyl}-3-piperidylcarbonyl]-3(S)-ethynyl-β-alanine ethyl ester hydrochloride (0.47 g) in N,N-dimethylformamide (5 ml) was added potassium carbonate (0.2 g) under stirring at 0° C. After stirring at 0° C. for 15 minutes, a solution of 4-bromomethyl-5-methyl-2-oxo-1,3-dioxole (0.19 g) in N,N-dimethylformamide (1 ml) was added to the mixture. After stirring at ambient temperature for overnight, the mixture was poured into saturated aqueous ammonium chloride, and extracted with ethyl acetate. The extract was washed with water and brine, and dried over MgSO4, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with (CHCl3:MeOH=100:1) to give N-[(R)-1-[3-{1-(5-methyl-2-oxo-1,3-dioxol-4-yl-methyl)-4-piperidyl}propionyl]-3-piperidylcarbonyl]-3(S)-ethynyl-β-alanine ethyl ester (90 mg) as an oil.

Workup

  1. stirringAfter stirring at 0° C. for 15 minutes
  2. stirringAfter stirring at ambient temperature for overnight
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with (CHCl3:MeOH=100:1)

Sources & evidence

ORD record
ord-5216db8c872e44838c2310b23aadff15
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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