Water → 8a-Hydroxy-3-(hydroxymethyl)-2,4',4',5'-tetramethyl-1,3',4-trioxooctahydro-8H-spiro[3,9a-epidithiocyclopenta[4,5]pyrrolo[1,2-a]pyrazine-7,2'-oxolan]-8-yl acetate

HRID 1579974Notes

Reaction equation

HRID 1579974 reaction equation
[CH3:1][CH:2]1[O:7][C@:6]2([C@@H:11]([O:12][C:13]([CH3:15])=[O:14])[C@:10]3([OH:31])[CH2:16][C@@:17]45[S:28]S[S:26][C@@:21]([CH2:29][OH:30])([N:22]([CH3:25])[C:23]4=[O:24])[C:19](=[O:20])[N:18]5[C@@H:9]3[CH2:8]2)[C:4](=[O:5])[C:3]1([CH3:33])[CH3:32].S(Cl)(Cl)=O.O>N1C=CC=CC=1>[CH3:1][CH:2]1[O:7][C:6]2([CH:11]([O:12][C:13]([CH3:15])=[O:14])[C:10]3([OH:31])[CH2:16][C:17]45[S:28][S:26][C:21]([CH2:29][OH:30])([N:22]([CH3:25])[C:23]4=[O:24])[C:19](=[O:20])[N:18]5[CH:9]3[CH2:8]2)[C:4](=[O:5])[C:3]1([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 101593100HCID 101593100, compound

Product 1

HCID 3255178a-Hydroxy-3-(hydroxymethyl)-2,4',4',5'-tetramethyl-1,3',4-trioxooctahydro-8H-spiro[3,9a-epidithiocyclopenta[4,5]pyrrolo[1,2-a]pyrazine-7,2'-oxolan]-8-yl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Sirodesmin C (5.0 mg.) in dry pyridine (0.1 ml.) was treated with thionyl chloride (0.01 ml.) for 10 minutes at 0°C., then added to iced-water (5 ml.) and left for 15 minutes. The solution was adjusted to pH 2 with 2N.sulphuric acid, then extracted with chloroform (3 × 5 ml.). The extracts were dried over sodium sulphate, then concentrated to yield Sirodesmin A as an oil (4.3 mg.).

Workup

  1. extractionsulphuric acid, then extracted with chloroform (3 × 5 ml.)
  2. dry with materialThe extracts were dried over sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5139d60f4b2241689bed2145e02a0ef4
Source dataset
uspto-grants-1976_01
Patent number
US03932394

Reaction notes

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