Hydrochloric Acid → HCID 86733225, compound

HRID 372617Notes

Reaction equation

HRID 372617 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-5hydroxy-6-methyl-2tetrahydropyranyl)-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 one 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 one hour the solvent was removed at reduced pressure
  6. customleaving an oil which

Sources & evidence

ORD record
ord-17ae667f0db04c97860defde55e16997
Source dataset
uspto-grants-1978_05
Patent number
USRE029651

Reaction notes

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