Triethylamine → HCID 18436785, compound

HRID 456472Notes

Reaction equation

HRID 456472 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][C:22]([NH2:25])([CH3:24])[CH3:23])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(CC)CC.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][C:22]([NH:25][S:34]([CH3:33])(=[O:36])=[O:35])([CH3:24])[CH3:23])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18436783HCID 18436783, compound

Product 1

HCID 18436785HCID 18436785, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound from Step 4 (175 mg, 0.5 mmol) and Et3N (210 uL, 1.5 mmol) in 5 mL of CH2Cl2 at 0° C. was added MsCl (41 uL, 0.53 mmol) at 10 uL increment until starting material was no longer present by TLC. The mixture was quenched with saturated aqueous sodium bicarbonate, diluted with EtOAc and washed with 1 M HCl, water and brine, which was then dried (Na2SO4), filtered and concentrated to afford about 155 mg (0.36 mmol, 73%) of N-boc-4-[2-(2-methanesulfonylamino-2-methyl-propoxy)-phenyl]-piperazine as a yellow solid. LRMS (electrospray): 428.1 [M+1].

Workup

  1. customThe mixture was quenched with saturated aqueous sodium bicarbonate
  2. additiondiluted with EtOAc
  3. washwashed with 1 M HCl, water and brine, which
  4. dry with materialwas then dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d20de5c19a934236a040eb6e697a2b5f
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

Loading…