Phosphoric Acid → HCID 19862586, compound

HRID 1165174Notes

Reaction equation

HRID 1165174 reaction equation
Cl.[CH2:2]([O:4][C:5]([CH2:7][NH:8][C:9]([O:11][C:12]1[C:17](=[O:18])[CH:16]=[CH:15][N:14]([CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH3:24])[C:13]=1[CH3:25])=[O:10])=[O:6])[CH3:3].Cl.C(N(CC)CC)C.P(=O)(O)(O)O.[Cl-].[Na+]>O>[CH2:2]([O:4][C:5]([CH2:7][NH:8][C:9]([O:11][C:12]1[C:17](=[O:18])[CH:16]=[CH:15][N:14]([CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH3:24])[C:13]=1[CH3:25])=[O:10])=[O:6])[CH3:3]

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 5234Sodium ChlorideHCID 11130Triethylamine hydrochlorideHCID 19862601HCID 19862601, compound

Product 1

HCID 19862586HCID 19862586, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4.0 g of the resultant 3-(ethoxycarbonylmethylaminocarbonyloxy)-1-(3-ethoxypropyl)-2-methyl-4(1H)-pyridinone hydrochloride, which melts at 92°-93° C. and is contaminated with a small amount of triethylamine hydrochloride, in 40 ml of water is adjusted to pH 2.5 with phosphoric acid, saturated with sodium chloride, and extracted with methylene chloride. The residue is recrystallised from a 95:5 mixture of ethyl acetate and methylene chloride, giving 3-(ethoxycarbonylmethylaminocarbonyloxy)-1-(3-ethoxypropyl)-2-methyl-4(1H)-pyridinone, which melts at 84°-85° C.

Workup

  1. extractionextracted with methylene chloride
  2. customThe residue is recrystallised from a 95:5 mixture of ethyl acetate and methylene chloride

Sources & evidence

ORD record
ord-799f0c25650a4161baaaa23bef46728d
Source dataset
uspto-grants-1990_03
Patent number
US04908371

Reaction notes

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