Hydrochloric Acid → HCID 136353518, compound

HRID 1605503Notes

Reaction equation

HRID 1605503 reaction equation
[NH2:1][C:2]1[C:10]([CH2:11][CH2:12][CH:13]([CH3:41])[CH:14]([OH:40])[CH:15]([CH3:39])[C:16](=[O:38])[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:6]([C:7]([OH:9])=[O:8])[C:5]([OH:42])=[C:4]([CH3:43])[CH:3]=1.CO.Cl.[N:47]([O-])=O.[Na+]>O.Cl[Cu]>[N+:1](=[C:2]1[C:10]([CH2:11][CH2:12][CH:13]([CH3:41])[CH:14]([OH:40])[CH:15]([CH3:39])[C:16](=[O:38])[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:6]([C:7]([OH:9])=[O:8])[C:5]([OH:42])=[C:4]([CH3:43])[CH2:3]1)=[N-:47]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 23277598HCID 23277598, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 136353518HCID 136353518, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent2×

Procedure

A solution of 5-amino-3-methyl-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}salicylic acid (1.28 g.) in 10 ml. methanol and 2 ml. of aqueous N HCl was cooled to 0° and a chilled solution of 150 mg. of NaNO2 in 1 ml. water was slowly added. To the solution was added 320 mg. of CuCl in 1 ml. of concentrated HCl. The reaction mixture was allowed to slowly warm up to room temperature and then diluted with water and extracted with ether. The ether extract was concentrated to a small volume and the crystallized product was collected by filtration, m.p. 137°-138°. [α]D -13.5° (0.7%, CH3OH).

Workup

  1. additionTo the solution was added 320 mg
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. concentrationwas concentrated to a small volume
  5. filtrationthe crystallized product was collected by filtration, m.p. 137°-138°

Sources & evidence

ORD record
ord-7103616808ce4bce9b6f171f17e68797
Source dataset
uspto-grants-1976_04
Patent number
US03950320

Reaction notes

Loading…