Hydrochloric Acid → HCID 86733225, compound

HRID 1605496Notes

Reaction equation

HRID 1605496 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]([CH3:42])[CH:14]([OH:41])[CH:15]([CH3:40])[C:16](=[N:38][OH:39])[CH:17]([CH2:36][CH3:37])[CH:18]2[CH:22]([CH3:23])[CH2:21][C:20]([CH2:34][CH3:35])([CH:24]3[CH2:29][CH2:28][C:27]([CH2:31][CH3:32])([OH:30])[CH:26]([CH3:33])[O:25]3)[O:19]2)=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[OH:43].[Na].Cl.[N+](=[CH2:48])=[N-]>C(Cl)Cl>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]([CH3:42])[CH:14]([OH:41])[CH:15]([CH3:40])[C:16](=[N:38][OH:39])[CH:17]([CH2:36][CH3:37])[CH:18]2[CH:22]([CH3:23])[CH2:21][C:20]([CH2:34][CH3:35])([CH:24]3[CH2:29][CH2:28][C:27]([CH2:31][CH3:32])([OH:30])[CH:26]([CH3:33])[O:25]3)[O:19]2)=[C:4]([C:5]([O:7][CH3:48])=[O:6])[C:3]=1[OH:43]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9550DiazomethaneHCID 5360545SodiumHCID 86733226HCID 86733226, compound

Product 1

HCID 86733225HCID 86733225, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.55 g of (-)-3-methyl-6-{7-ethyl-4-hydroxy-6-hydroxyimino-3,5-dimethyl-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]heptyl}salicylic acid, sodium salt in 100 ml methylene chloride was treated with 1N HCl. The solvent layer was separated, washed with water and concentrated under reduced pressure to a solid. A portion (1.3 g) of the solid, equal to 2.15 millimole, was dissolved in ether and treated with 4.25 millimole of an ethereal solution of diazomethane. At the end of 1 hour the solvent was removed at reduced pressure leaving an oil which upon standing under a high vacuum solidified to yield 3-methyl-6-{7-ethyl-4-hydroxy-6-hydroxyimino-3,5-dimethyl-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]heptyl}salicylic acid, methyl ester, isomer A; [α]D25 + 5.77° (1.03%, CH3OH).

Workup

  1. customThe solvent layer was separated
  2. washwashed with water
  3. concentrationconcentrated under reduced pressure to a solid
  4. dissolutionA portion (1.3 g) of the solid, equal to 2.15 millimole, was dissolved in ether
  5. customAt the end of 1 hour the solvent was removed at reduced pressure
  6. customleaving an oil which

Sources & evidence

ORD record
ord-c79f85b3c12045d7959a33c70ca381e1
Source dataset
uspto-grants-1976_04
Patent number
US03950320

Reaction notes

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