Triethylamine → HCID 57850366, compound

HRID 445090Notes

Reaction equation

HRID 445090 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[CH2:9][CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][CH:8]([CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[CH2:9][CH2:10][O:11][S:27]([CH3:26])(=[O:29])=[O:28])=[O:18])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 24729731HCID 24729731, compound

Product 1

HCID 57850366HCID 57850366, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-hydroxy-1-(tetrahydro-pyran-4-yl)-propyl]-carbamic acid tert-butyl ester (0.200 g, 0.770 mmol) and NEt3 (192 μL, 0.920 mmol) in CH2Cl2 (8 mL) was added MsCl (72 μL, 0.92 mmol) at 0° C. and the mixture was stirred at room temperature for 10 h. The solvent was evaporated to dryness and EtOAC was added. The ethyl acetate layer was washed with aq. NaHCO3, dried (Na2SO4), filtered, and solvent was evaporated under reduced pressure to afford methanesulfonic acid 3-tert-butoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-propyl ester (0.162 g). LC-MS [M+Na] 360.2. The product was sufficiently pure for the next step and used without further purification.

Workup

  1. customThe solvent was evaporated to dryness and EtOAC
  2. additionwas added
  3. washThe ethyl acetate layer was washed with aq. NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customsolvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2dc8def7818046cab7b49bac1ce4c475
Source dataset
uspto-grants-2013_07
Patent number
US08476285B2

Reaction notes

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