Triethylamine → HCID 90177059, compound

HRID 1499298Notes

Reaction equation

HRID 1499298 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[C:13]([O:16][C@@H:17]1[C@@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:21]([O:27][C:28](=[O:30])[CH3:29])[C@@H:20]([S:31][CH3:32])[O:19][C@H:18]1[C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[C:35]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][CH2:49][CH2:50][OH:51])=[CH:43][CH:42]=2)[CH:34]=1)(=[O:15])[CH3:14]>C(Cl)Cl>[C:13]([O:16][C@@H:17]1[C@@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:21]([O:27][C:28](=[O:30])[CH3:29])[C@@H:20]([S:31][CH3:32])[O:19][C@H:18]1[C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[C:35]([CH2:40][C:41]2[CH:42]=[CH:43][C:44]([CH2:47][CH2:48][CH2:49][CH2:50][O:51][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:45][CH:46]=2)[CH:34]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 90183094HCID 90183094, compound

Product 1

HCID 90177059HCID 90177059, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (41 μL, 0.53 mmol) and triethylamine (80 μL, 0.58 mmol) were added to a solution of (2S,3S,4R,5S,6R)-2-(3-(4-(4-hydroxybutyl)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (22, 247 mg, 0.44 mmol) in 5 mL CH2Cl2 and stirred at room temperature for 2 hours. The reaction was quenched with 1N aqueous HCl. The aqueous layer was extracted two times with EtOAc. The combined organic layers were washed with H2O and brine, dried with MgSO4, filtered, and concentrated in vacuo to provide the product 23 (279 mg, 99% yield), which was used in the next step without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.14 (s, 2 H), 7.02-7.11 (m, 3 H), 7.00 (d, J=7.8 Hz, 2 H), 5.33 (dd, J=9.6 Hz, 1 H), 5.21 (dd, J=9.6 Hz, 1 H), 5.12 (dd, J=9.6 Hz, 1 H), 4.48-4.56 (m, 1 H), 4.39 (d, J=9.9 Hz, 1 H), 4.24 (t, J=6.1 Hz, 1 H), 3.93 (d, J=3.8 Hz, 2 H), 2.99 (s, 3 H), 2.62 (t, J=7.2 Hz, 2H), 2.22 (s, 3 H), 2.15-2.20 (m, 3 H), 2.10 (s, 3 H), 2.01 (s, 3 H), 1.70-1.81 (m, 4 H). MS (ES+) [M+NH4]+=654.

Workup

  1. customThe reaction was quenched with 1N aqueous HCl
  2. extractionThe aqueous layer was extracted two times with EtOAc
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9227e31d2ea94a30811932153b36af3a
Source dataset
uspto-grants-2015_12
Patent number
US09200025B2

Reaction notes

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