Triethylamine → HCID 66654206, compound

HRID 2036230Notes

Reaction equation

HRID 2036230 reaction equation
C([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@H:9]1[C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=O)(C)(C)C.[CH3:31][CH2:32]N(CC)CC.C(Cl)(=O)C=C>C(Cl)Cl.Cl.O1CCOCC1>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][O:24][C:18]1[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:17]=1[CH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][N:8]1[C:6](=[O:5])[CH:31]=[CH2:32])[CH3:30]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 66654185HCID 66654185, compound

Product 1

HCID 66654206HCID 66654206, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To an ice-cooled solution of (S)-1-(5-chloro-2-ethoxycarbonylmethoxy-phenyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (2.16 g, 5.0 mmol, 1.0 eq.) in DCM (100 mL), 4M HCl in dioxane (25 mL) was added. The resulting solution was stirred at r.t. for 18 hours. The reaction mixture was concentrated in vacuo. To a solution of the residue and NEt3 (3.48 mL, 25 mmol, 5.0 eq.) in DCM (100 mL), acryloyl chloride (0.45 mL, 5.5 mmol, 1.1 eq.) was added. The resulting solution was stirred at r.t. for 2 hours. The reaction mixture was concentrated in vacuo. The residue was purified by flash master (column: 100 g, flow: 45 mL/min, Heptane+20% AcOEt to Heptane+70% AcOEt) to give the title compound.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. stirringThe resulting solution was stirred at r.t. for 2 hours
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customThe residue was purified by flash master (column: 100 g, flow: 45 mL/min, Heptane+20% AcOEt to Heptane+70% AcOEt)

Sources & evidence

ORD record
ord-63c15a6452b34afb8c039794e92de90b
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

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