Triethylamine → HCID 86718369, compound

HRID 1518761Notes

Reaction equation

HRID 1518761 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C@@H:6]([N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C@H:7]([CH3:10])[CH2:8][OH:9].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[CH3:27][S:28]([O:9][CH2:8][C@@H:7]([CH3:10])[C@H:6]([N:11]([C:12]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:18])[CH3:19])[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86718354HCID 86718354, compound

Product 1

HCID 86718369HCID 86718369, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl ((1S,2S)-1-(furan-2-yl)-3-hydroxy-2-methylpropyl)(methyl)-carbamate (108 mg, 0.40 mmol) in DCM (2 mL) at 0° C. was added triethylamine (81 mg, 0.112 ml, 0.80 mmol, 2 equiv) followed by methanesulfonylchloride (55 mg, 0.037 ml, 0.48 mmol, 1.2 equiv) and the solution was stirred at 0° C. for 1 hour. The solution was diluted with 10 mL DCM and washed with sat. NH4Cl solution, water and brine. After drying over MgSO4 the solution was concentrated in vacuo to give crude product 2.16a (140 mg, 99% yield). 1H NMR (CDCl3, 400 MHz) 7.38 (dd, J=1.76, 0.98 Hz, 1H) 6.35 (dd, J=3.13, 1.96 Hz, 1H) 6.31 (br. s., 1H) 5.29-5.32 (m, 1H) 4.16 (dd, J=9.98, 3.33 Hz, 1H) 3.90 (br. s., 1H) 2.89-2.96 (m, 3H) 2.68-2.75 (m, 3H) 2.55-2.67 (m, 1H) 1.48 (br. s., 9H) 1.11 (d, J=6.65 Hz, 3H)

Workup

  1. washwashed with sat. NH4Cl solution, water and brine
  2. dry with materialAfter drying over MgSO4 the solution
  3. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-25a1440e8b364679bf1e71bae67276b9
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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