Hydroxyamine hydrochloride → HCID 178449945, compound

HRID 372616Notes

Reaction equation

HRID 372616 reaction equation
[CH3:1][CH2:2][C@@H:3]([C:22]([C@H:24]([C@@H:26]([OH:42])[C@@H:27]([CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[C:33]([OH:38])[C:32]=1[C:39]([OH:41])=[O:40])[CH3:28])[CH3:25])=O)[C@H:4]1[O:8][C@@:7]([C@@H:11]2[O:16][C@@H:15]([CH3:17])[C@@:14]([OH:20])([CH2:18][CH3:19])[CH2:13][CH2:12]2)([CH2:9][CH3:10])[CH2:6][C@@H:5]1[CH3:21].Cl.[NH2:44][OH:45]>C(O)C>[OH:45][NH3+:44].[CH3:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][CH2:29][CH:27]([CH3:28])[CH:26]([OH:42])[CH:24]([CH3:25])[C:22](=[N:44][OH:45])[CH:3]([CH2:2][CH3:1])[CH:4]2[CH:5]([CH3:21])[CH2:6][C:7]([CH2:9][CH3:10])([CH:11]3[CH2:12][CH2:13][C:14]([CH2:18][CH3:19])([OH:20])[CH:15]([CH3:17])[O:16]3)[O:8]2)=[C:32]([C:39]([O-:41])=[O:40])[C:33]=1[OH:38]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 5360807Lasalocid

Product 1

HCID 178449945HCID 178449945, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10 g of crystalline antibiotic X-537A and 5 g of hydroxylamine hydrochloride in 50 ml ethanol containing 5 ml pyridine was heated under reflux for 60 hours. The solution was evaporated to dryness and 5 ml water added. The solid product was triturated and filtered, then recrystallized from aqueous ethanol to give (-)-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-tetrahydro-pyranyl)-2-tetrahydrofuryl]heptyl} salicylic acid, hydroxylammonium salt; m.p. 168°-170°, [α]D25 -12.34° (1%, DMSO).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 60 hours
  3. customThe solution was evaporated to dryness and 5 ml water
  4. additionadded
  5. customThe solid product was triturated
  6. filtrationfiltered
  7. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-d2e7b68a77404508a01b8788600fb3a0
Source dataset
uspto-grants-1978_05
Patent number
USRE029651

Reaction notes

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