Chloroform → HCID 23277600, compound

HRID 1605504Notes

Reaction equation

HRID 1605504 reaction equation
[Na].[CH3:2][CH2:3][C@@H:4]([C:23]([C@H:25]([C@@H:27]([OH:43])[C@@H:28]([CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[C:34]([OH:39])[C:33]=1[C:40]([OH:42])=[O:41])[CH3:29])[CH3:26])=[O:24])[C@H:5]1[O:9][C@@:8]([C@@H:12]2[O:17][C@@H:16]([CH3:18])[C@@:15]([OH:21])([CH2:19][CH3:20])[CH2:14][CH2:13]2)([CH2:10][CH3:11])[CH2:7][C@@H:6]1[CH3:22].C(Cl)(Cl)[Cl:45].ClCl>C(Cl)(Cl)(Cl)Cl>[Cl:45][C:37]1[C:32]([CH2:31][CH2:30][CH:28]([CH3:29])[CH:27]([OH:43])[CH:25]([CH3:26])[C:23](=[O:24])[CH:4]([CH2:3][CH3:2])[CH:5]2[CH:6]([CH3:22])[CH2:7][C:8]([CH2:10][CH3:11])([CH:12]3[CH2:13][CH2:14][C:15]([CH2:19][CH3:20])([OH:21])[CH:16]([CH3:18])[O:17]3)[O:9]2)=[C:33]([C:40]([OH:42])=[O:41])[C:34]([OH:39])=[C:35]([CH3:38])[CH:36]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 24526ChlorineHCID 5360545SodiumHCID 5360807Lasalocid

Product 1

HCID 23277600HCID 23277600, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a cold solution (~3°) of 6.12 g. of the sodium salt of antibiotic X-537A in 50 ml. of chloroform/3 ml. of carbon tetrachloride was slowly added 34 ml. of carbon tetrachloride saturated with 10 millimoles of chlorine gas. The reaction was continued for 1/2 hour after which the solution was filtered and the filtrate treated with a saturated aqueous solution of Na2CO3. The solvent layer was dried over Na2SO4 and concentrated to a small volume from which after addition of hexane the crystalline product was recovered. The crystalline material which had a tendency to incorporate the solvent of crystallization was twice recrystallized from methylene chloride/ether and acetone/hexane, m.p. 183°-185°, [α]D25 -44.31° (C, 0.99%, CHCl3).

Workup

  1. customTo a cold solution (~3°) of 6.12 g
  2. filtrationafter which the solution was filtered
  3. additionthe filtrate treated with a saturated aqueous solution of Na2CO3
  4. dry with materialThe solvent layer was dried over Na2SO4
  5. concentrationconcentrated to a small volume from which
  6. additionafter addition of hexane the crystalline product
  7. customwas recovered
  8. customthe solvent of crystallization
  9. customwas twice recrystallized from methylene chloride/ether and acetone/hexane, m.p. 183°-185°, [α]D25 -44.31° (C, 0.99%, CHCl3)

Sources & evidence

ORD record
ord-c44d581683ce44a3a4f443700a570105
Source dataset
uspto-grants-1976_04
Patent number
US03950320

Reaction notes

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