Triethylamine → [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[4-methyl-3-[[4-[(E)-4-methylsulfonyloxybut-1-enyl]phenyl]methyl]indol-1-yl]tetrahydropyran-2-yl]methyl acetate

HRID 2284528Notes

Reaction equation

HRID 2284528 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:8]([N:24]2[C:32]3[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=3)[C:26]([CH2:34][C:35]3[CH:40]=[CH:39][C:38](/[CH:41]=[CH:42]/[CH2:43][CH2:44][OH:45])=[CH:37][CH:36]=3)=[CH:25]2)[O:7]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:53][S:54](Cl)(=[O:56])=[O:55]>ClCCl>[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:8]([N:24]2[C:32]3[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=3)[C:26]([CH2:34][C:35]3[CH:36]=[CH:37][C:38](/[CH:41]=[CH:42]/[CH2:43][CH2:44][O:45][S:54]([CH3:53])(=[O:56])=[O:55])=[CH:39][CH:40]=3)=[CH:25]2)[O:7]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 118021778[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[[4-[(E)-4-hydroxybut-1-enyl]phenyl]methyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate

Product 1

HCID 118021852[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[4-methyl-3-[[4-[(E)-4-methylsulfonyloxybut-1-enyl]phenyl]methyl]indol-1-yl]tetrahydropyran-2-yl]methyl acetateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[[4-[(E)-4-hydroxybut-1-enyl]phenyl]methyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate (1.2 mmol) in dichloromethane (50 mL) and triethylamine (3.6 mmol) at room temperature, add methanesulfonyl chloride (1.56 mmol) dropwise over 5 minutes. Stir at room temperature for 1 hour, then dilute the reaction with dichloromethane (100 mL). Wash the organics with water (2×100 mL) followed by brine (100 mL). Dry the organics over sodium sulfate, filter, and concentrate under reduced pressure to yield the title compound as a light yellow foam (0.84g, 1.2 mmol). Use this material in the next step (Scheme II, step B) without further purification.

Workup

  1. additiondilute
  2. washWash the organics with water (2×100 mL)
  3. dry with materialDry the organics over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-42b254ee8ac74bdd9acc4c85f69384e5
Source dataset
uspto-grants-2015_09
Patent number
US09145435B2

Reaction notes

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