Hydrochloric Acid → HCID 136463331, compound

HRID 1605499Notes

Reaction equation

HRID 1605499 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[N:9]([O-])=O.[Na+].[CH3:13][CH2:14][C@@H:15]([C:34]([C@H:36]([C@@H:38]([OH:54])[C@@H:39]([CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([CH3:49])=[C:45]([OH:50])[C:44]=1[C:51]([OH:53])=[O:52])[CH3:40])[CH3:37])=[O:35])[C@H:16]1[O:20][C@@:19]([C@@H:23]2[O:28][C@@H:27]([CH3:29])[C@@:26]([OH:32])([CH2:30][CH3:31])[CH2:25][CH2:24]2)([CH2:21][CH3:22])[CH2:18][C@@H:17]1[CH3:33]>O>[C:2]1([N:1]=[N:9][C:48]2[C:43]([CH2:42][CH2:41][CH:39]([CH3:40])[CH:38]([OH:54])[CH:36]([CH3:37])[C:34](=[O:35])[CH:15]([CH2:14][CH3:13])[CH:16]3[CH:17]([CH3:33])[CH2:18][C:19]([CH2:21][CH3:22])([CH:23]4[CH2:24][CH2:25][C:26]([CH2:30][CH3:31])([OH:32])[CH:27]([CH3:29])[O:28]4)[O:20]3)=[C:44]([C:51]([OH:53])=[O:52])[C:45]([OH:50])=[C:46]([CH3:49])[CH:47]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 5360807LasalocidHCID 23668193Sodium Nitrite

Product 1

HCID 136463331HCID 136463331, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 0.18 ml. of aniline in 8 ml. of N HCl, cooled to 0°-5°C. in an ice bath was slowly added 150 mg. of NaNO2 in water chilled to the same temperature. To the above solution was added a cold methanolic solution of 550 mg. of crystalline antibiotic X-537A. The reaction mixture was kept at 3° to 5° for 15 minutes and then allowed to slowly reach room temperature. At the end of 2 hours, the reaction mixture was diluted with water and extracted with ethyl acetate. The solvent extract was washed with a saturated solution of Na2CO3, dried over NaSO4 and concentrated to a solid. The solid was chromatographed on a 30 g. silica gel (Grade 62) column eluting with a gradient between 300 ml. methylene chloride and 500 ml. ether. The product was eluted in the first peak and crystallized from methylene chloride/hexane, m.p. 212°-215°, [α] D25 -27.30° (0.586%, CH3OH).

Workup

  1. additionTo the above solution was added a cold methanolic solution of 550 mg
  2. customallowed to slowly reach room temperature
  3. extractionextracted with ethyl acetate
  4. extractionThe solvent extract
  5. washwas washed with a saturated solution of Na2CO3
  6. dry with materialdried over NaSO4
  7. concentrationconcentrated to a solid
  8. customThe solid was chromatographed on a 30 g
  9. washsilica gel (Grade 62) column eluting with a gradient between 300 ml
  10. washThe product was eluted in the first peak
  11. customcrystallized from methylene chloride/hexane, m.p. 212°-215°, [α] D25 -27.30° (0.586%, CH3OH)

Sources & evidence

ORD record
ord-85f750977b304efebfe2189d9c124f7b
Source dataset
uspto-grants-1976_04
Patent number
US03950320

Reaction notes

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