D-1,4-Dithiothreitol → HCID 56948309, compound

HRID 2406570Notes

Reaction equation

HRID 2406570 reaction equation
[CH3:1][CH2:2][CH2:3][C@H:4]([NH:11][C:12](/[C:14](/[C:23]#[N:24])=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[N:17]=1)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[SH:25][CH2:26][C@H:27]([C@@H:29]([CH2:31][SH:32])[OH:30])[OH:28]>C(#N)C.C(OCC)(=O)C>[Br:22][C:18]1[N:17]=[C:16]([CH:15]([S:25][CH2:26][CH:27]([OH:28])[CH:29]([OH:30])[CH2:31][SH:32])[CH:14]([C:23]#[N:24])[C:12]([NH:11][CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:3][CH2:2][CH3:1])=[O:13])[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 446094D-1,4-DithiothreitolHCID 11222830WP1130

Product 1

HCID 56948309HCID 56948309, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of WP1130 (18; 0.05 g, 0.13 mmol) in acetonitrile (6 mL) was added to a stirred solution of dithiothreitol (2 g, 13 mmol) in acetonitrile (13 mL) at room temp. After 20 hours TLC [Hxa/EtOAc 1:1] showed a single product and no starting material. The mixture was filtered through a short column of silica gel in acetonitrile, and the filtrate stripped of solvent under reduced pressure. A colorless syrup was obtained. The syrup was dissolved in ethyl acetate and flash chromatographed on a column (35×70 mm) of silica gel in ethyl acetate to afford a clear yellow oil (0.02 g) which began to crystallize upon standing. Mass spec ES+; m/z=560, 562 (m+23) and 538, 540 (m+1).

Workup

  1. filtrationThe mixture was filtered through a short column of silica gel in acetonitrile
  2. customA colorless syrup was obtained
  3. customflash chromatographed on a column (35×70 mm) of silica gel in ethyl acetate

Sources & evidence

ORD record
ord-462afbbc0c1c47f5a81f0f4339d5a4b2
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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