Water → Sodium

HRID 372618Notes

Reaction equation

HRID 372618 reaction equation
[Na:1].[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:44](Cl)(=[O:47])[CH2:45][CH3:46].O>N1C=CC=CC=1>[CH3:38][C:35]1[C:34]([O:39][C:44](=[O:47])[CH2:45][CH3:46])=[C:33]([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)=[CH:37][CH:36]=1)[C:40]([OH:42])=[O:41].[Na:1]

Participants

7

Reactant 4

HCID 962WaterHCID 62324Propionyl chlorideHCID 5360545SodiumHCID 5360807Lasalocid

Product 2

HCID 5360545SodiumHCID 20329630HCID 20329630, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6.12 g. of the sodium salt of antibiotic X-537A was dissolved in pyridine (10 ml.) by warming slightly. The solution was cooled in an ice bath and treated with propionyl chloride, then allowed to stand at room temperature for 2 hours. The mixture was poured into water, extracted with ethyl acetate, and the organic phase washed in succession with 1N hydrochloric acid (several times) and sodium carbonate solution (twice). Evaporation of the ethyl acetate solution left a residue which was crystallized from methylene chloride/hexane to afford 3-methyl-2-propionyloxy-6-{7-ethyl-4-hydroxy-3,5-dimethyl-6-oxo- 7[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]heptyl}benzoic acid, sodium salt, m.p. 185°-186.5° [α]D25 -20.00° (C=1.00 in methanol).

Workup

  1. temperatureby warming slightly
  2. temperatureThe solution was cooled in an ice bath
  3. extractionextracted with ethyl acetate
  4. washthe organic phase washed in succession with 1N hydrochloric acid (several times) and sodium carbonate solution (twice)
  5. customEvaporation of the ethyl acetate solution
  6. waitleft a residue which
  7. customwas crystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-061121e73f004242a81b627c5a9b2421
Source dataset
uspto-grants-1978_05
Patent number
USRE029651

Reaction notes

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