Hydrochloric Acid → HCID 59558423, compound

HRID 1175157Notes

Reaction equation

HRID 1175157 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6](Cl)=[O:7])[CH3:2].[CH2:10]([O:12][C:13]([C:15]1([C:18]2([NH2:21])[CH2:20][CH2:19]2)[CH2:17][CH2:16]1)=[O:14])[CH3:11].C(N(CC)CC)C.Cl>C(Cl)Cl>[CH2:10]([O:12][C:13]([C:15]1([C:18]2([NH:21][C:6](=[O:7])[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:9])[CH2:20][CH2:19]2)[CH2:17][CH2:16]1)=[O:14])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 11332703546114-00-5

Product 1

HCID 59558423HCID 59558423, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chlorocarbonyl-acetic acid ethyl ester (1.24 ml; 11.2 mmol) in CH2Cl2 (5 ml) is added dropwise under stirring within 15 minutes at room temperature to a solution of 1′-amino-bicyclopropyl-1-carboxylic acid ethyl ester (1.38 g; 8.16 mmol) (Synlett. 2003, 2, 265) and triethylamine (1.02 ml; 10.4 mmol) in CH2Cl2 (100 ml). Stirring is continued for 5 minutes, then the reaction mixture is poured on water, acidified with 2N HCl and extracted with CH2Cl2 three times. The combined organic phases are dried over Na2SO4, filtered and evaporated to dryness. The combined organic phases are dried over Na2SO4, filtered, evaporated and purified via chromatography (SiO2; acetone/heptane 9:92>2/8) to yield the title compound as off-white crystals (1.9 g; 79%).

Workup

  1. additionthe reaction mixture is poured on water
  2. extractionextracted with CH2Cl2 three times
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. dry with materialThe combined organic phases are dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. custompurified via chromatography (SiO2; acetone/heptane 9:92>2/8)

Sources & evidence

ORD record
ord-cde24668f26046afb8407c1461c1c709
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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