Triethylamine → HCID 57410217, compound

HRID 527689Notes

Reaction equation

HRID 527689 reaction equation
[CH3:1][C:2]1([CH3:24])[C:6]2[C:7]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:23])[C@@H:20]([CH3:22])[NH2:21])=[CH:14][CH:13]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.C(N(CC)CC)C.Cl[C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[CH3:24][C:2]1([CH3:1])[C:6]2[C:7]([O:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[C:19](=[O:23])[C@@H:20]([CH3:22])[NH:21][C:33]4=[O:35])=[CH:14][CH:13]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 67966845HCID 67966845, compound2×

Product 1

HCID 57410217HCID 57410217, compoundYield 140.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N1-{4-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]phenyl}-D-alaninamide (Intermediate 57, 66 mg) in dichloromethane (20 ml, SCRC) was added triethylamine (0.085 ml, 0.607 mmol, SCRC). Triphosgene (24.00 mg, 0.081 mmol, SCRC) was added dropwise at 0° C. and the reaction mixture was stirred at room temperature for 0.5 hours. The mixture was quenched with water (20 ml) and it was extracted with dichloromethane (3 times 50 ml, SCRC). The combined organic layers were dried, evaporated and purified by column chromatography on silica gel with EtAc/PE (1/30) as eluents to afford the title compound as a white solid (40 mg).

Workup

  1. customThe mixture was quenched with water (20 ml) and it
  2. extractionwas extracted with dichloromethane (3 times 50 ml, SCRC)
  3. customThe combined organic layers were dried
  4. customevaporated
  5. custompurified by column chromatography on silica gel with EtAc/PE (1/30) as eluents

Sources & evidence

ORD record
ord-7508a43890b546cf87c5aa9351909e14
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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