Water → HCID 87170972, compound

HRID 2406571Notes

Reaction equation

HRID 2406571 reaction equation
[SH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[CH3:7][CH2:8][CH2:9][C@H:10]([NH:17][C:18](/[C:20](/[C:29]#[N:30])=[CH:21]/[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[N:23]=1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.ClCCl>C(#N)C>[Br:28][C:24]1[N:23]=[C:22]([CH:21]([S:1][CH2:2][CH:3]([OH:4])[CH2:5][OH:6])[CH:20]([C:29]#[N:30])[C:18]([NH:17][C@H:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:9][CH2:8][CH3:7])=[O:19])[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 7291ThioglycerolHCID 11222830WP1130

Product 1

HCID 87170972HCID 87170972, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Thioglycerol (42 μL, 0.5 mmol) was added to a stirred solution of WP1130 (19 mg, 0.05 mmol) in acetonitrile (0.5 mL). The resulting mixture was stirred at room temperature for 17 hours. The mixture was distributed between water and dichloromethane. The separated organic layer was washed with sat. brine, dried over sodium sulfate, and concentrated to an oil. Purification by preparative TLC eluting with hexanes/ethyl acetate (6:4) afforded 20 (20 mg, 82%) as a clear oil: MS (ES+) m/z 492.0 (M+H)+.

Workup

  1. washThe separated organic layer was washed with sat. brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to an oil
  4. customPurification by preparative TLC
  5. washeluting with hexanes/ethyl acetate (6:4)

Sources & evidence

ORD record
ord-e874a45f3fdf4c8691a81f41f88da8e6
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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