3-Pyridinecarbonyl chloride, hydrochloride (1:1) → HCID 20326282, compound

HRID 372619Notes

Reaction equation

HRID 372619 reaction equation
[Na].[CH3:2][CH2:3][C@@H:4]([C:23]([C@H:25]([C@@H:27]([OH:43])[C@@H:28]([CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[C:34]([OH:39])[C:33]=1[C:40]([OH:42])=[O:41])[CH3:29])[CH3:26])=[O:24])[C@H:5]1[O:9][C@@:8]([C@@H:12]2[O:17][C@@H:16]([CH3:18])[C@@:15]([OH:21])([CH2:19][CH3:20])[CH2:14][CH2:13]2)([CH2:10][CH3:11])[CH2:7][C@@H:6]1[CH3:22].Cl.[C:45](Cl)(=[O:52])[C:46]1[CH:51]=[CH:50][CH:49]=[N:48][CH:47]=1>N1C=CC=CC=1>[NH4+:48].[CH3:38][C:35]1[C:34]([O:39][C:45](=[O:52])[C:46]2[CH:51]=[CH:50][CH:49]=[N:48][CH:47]=2)=[C:33]([C:32]([CH2:31][CH2:30][CH:28]([CH3:29])[CH:27]([OH:43])[CH:25]([CH3:26])[C:23](=[O:24])[CH:4]([CH2:3][CH3:2])[CH:5]2[CH:6]([CH3:22])[CH2:7][C:8]([CH2:10][CH3:11])([CH:12]3[CH2:13][CH2:14][C:15]([CH2:19][CH3:20])([OH:21])[CH:16]([CH3:18])[O:17]3)[O:9]2)=[CH:37][CH:36]=1)[C:40]([O-:42])=[O:41]

Participants

5

Reactant 3

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 5360545SodiumHCID 5360807Lasalocid

Product 1

HCID 20326282HCID 20326282, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of the sodium salt of antibiotic X-537A (6.12 g.) in pyridine (10 ml.) was stirred at room temperature under nitrogen with 3 g. of nicotinoyl chloride hydrochloride for 13 days. Extraction and purification as in Example 22 gave a yellow residue which resisted crystallization. Attempted crystallization from hexane gave a gum which was dried on a clay plate to an amorphous solid, m.p. 81°-92° (dec.) [α]D25 -14.64° (C=1.04 in methanol).

Workup

  1. extractionExtraction and purification as in Example 22
  2. customgave a yellow residue which
  3. customcrystallization
  4. customAttempted crystallization from hexane
  5. customgave a gum which
  6. dry with materialwas dried on a clay plate to an amorphous solid, m.p. 81°-92° (dec.) [α]D25 -14.64° (C=1.04 in methanol)

Sources & evidence

ORD record
ord-90c97ce8794b45cb87c542c71a825d94
Source dataset
uspto-grants-1978_05
Patent number
USRE029651

Reaction notes

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