Triethylamine → HCID 90093768, compound

HRID 1753105Notes

Reaction equation

HRID 1753105 reaction equation
Cl.[CH2:2]([O:4][C:5](=[NH:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:3].C(N(CC)CC)C.[C:20](Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]>ClCCl>[CH3:22][C:21]([CH3:24])([CH3:23])[C:20]([N:12]=[C:5]([O:4][CH2:2][CH3:3])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochloride

Product 1

HCID 90093768HCID 90093768, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

Ethyl 3-Ethoxy-3-iminopropanoate Hydrochloride (Preparation 118, 50 g, 0.256 mol) was suspended in dichloromethane (600 mL). The suspension was cooled to −15° C. and triethylamine (7.8 mL, 0.56 mol) followed by pivaloyl chloride (31.5 mL, 0.256 mol) were added. The reaction mixture was left for 18 hours at room temperature, then washed with water, dried over MgSO4, and evaporated. The residue was triturated with hexane. The resulting precipitate was filtered and dried to afford the title compound (44 g, 70%). Taken directly on to the next step.

Workup

  1. additionwere added
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was triturated with hexane
  6. filtrationThe resulting precipitate was filtered
  7. customdried

Sources & evidence

ORD record
ord-a501077e27a9423eaeb43fe34d9588f5
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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