Hydrochloric Acid → HCID 66970799, compound

HRID 1360640Notes

Reaction equation

HRID 1360640 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([S:12]([CH2:15][CH:16]([C@H:18]3[CH2:22][CH2:21][CH2:20][O:19]3)O)(=[O:14])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.CCN(CC)CC.CS(Cl)(=O)=O.Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([S:12]([CH:15]=[CH:16][C@H:18]3[CH2:22][CH2:21][CH2:20][O:19]3)(=[O:14])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57855478HCID 57855478, compound

Product 1

HCID 66970799HCID 66970799, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-[(7-chloro-3,4-dihydroisoquinolin-2(1H)-yl)sulfonyl]-1-[(2R)-tetrahydrofuran-2-yl]ethanol (420 mg, 1.21 mmol) and Et3N (370 mg, 3.63 mmol) in anhydrous DCM (5 ml) was cooled at 0° C., then methanesulfonyl chloride (0.14 ml, 1.82 mmol) was added dropwise. The resulting mixture was stirred at 0° C. for 5 min., then at RT for 15 hours. The reaction mixture was poured into a 1N aqueous solution of HCl and extracted with EtOAc (2×). The organic layers were combined, dried (MgSO4) and the solvents were removed under reduced pressure to give the title compound as an orange solid (400 mg, quantitative). HPLC, Rt: 3.7 min (purity: 94.2%). LC/MS, M+(ESI): 328.2.

Workup

  1. waitat RT for 15 hours
  2. extractionextracted with EtOAc (2×)
  3. dry with materialdried (MgSO4)
  4. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-1772c0fae62b45bd879a68506be72030
Source dataset
uspto-grants-2011_02
Patent number
US07879876B2

Reaction notes

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