Triethylamine → HCID 90241901, compound

HRID 1777180Notes

Reaction equation

HRID 1777180 reaction equation
[CH2:1]1[C:10]2[C:5](=[C:6]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.CCN(CC)CC.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[CH3:25][S:26]([N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:1]1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 90241000HCID 90241000, compound

Product 1

HCID 90241901HCID 90241901, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of ethyl 2-((1,2,3,4-tetrahydroisoquinolin-5-yl)oxy)acetate (300 mg, 1.28 mmol) and Et3N (387 mg, 3.83 mmol) in DCM (25 mL) cooled in an ice-water bath was added MsCl (176.6 mg, 1.54 mmol) drop wise. The mixture was stirred at 25° C. for 16 h and then quenched with aq. NH4Cl. The mixture was extracted with ethyl acetate and the combined organic layers were concentrated under vacuum to give the crude product (312 mg, 78%) which was used to the next step without purification.

Workup

  1. customquenched with aq. NH4Cl
  2. extractionThe mixture was extracted with ethyl acetate
  3. concentrationthe combined organic layers were concentrated under vacuum

Sources & evidence

ORD record
ord-74cc9b2d33ad43d681051ac006fd2223
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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