Hydrochloric Acid → HCID 18434254, compound

HRID 1636742Notes

Reaction equation

HRID 1636742 reaction equation
[CH2:1]([N:4]([CH3:33])[CH2:5]/[CH:6]=[CH:7]/[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:31])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27]C(=O)C)=[CH:12][C:11]=1[F:32])[CH:2]=[CH2:3].Cl>C(O)C>[CH2:1]([N:4]([CH3:33])[CH2:5]/[CH:6]=[CH:7]/[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:31])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH2:27])=[CH:12][C:11]=1[F:32])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid3×HCID 18434229HCID 18434229, compound

Product 1

HCID 18434254HCID 18434254, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.84 g of (E)-N-[11-[4-[4-(allyl-methyl-amino)-but-2-enyloxy]-3-fluoro-phenyl]-11-oxo-undecyl]-acetamide (Ex. 4c) in 30 ml of ethanol/5 ml of 18% aqueous hydrochloric acid is boiled for 7 hrs. and, after the addition of 4 ml of concentrated hydrochloric acid, boiled for 24 hrs. and, after the addition of a further 4 ml of concentrated hydrochloric acid, boiled for 30 hrs. After concentration the residue is taken up in 10% potassium hydrogen sulphate solution/methylene chloride and the aqueous phase is made basic with 10% sodium hydroxide solution and extracted with methylene chloride. The organic phase is dried and concentrated. There are obtained 1.48 g of (E)-1-[4-[4-(allyl-methyl-amino)-but-2-enyloxy]-3-fluoro-phenyl]-11-amino-undecan-1-one which is converted into the fumarate, MS: m/e 419 (M+H+).

Workup

  1. waitboiled for 30 hrs
  2. concentrationAfter concentration the residue
  3. extractionextracted with methylene chloride
  4. customThe organic phase is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6bae2aacd5c64439b02c4c4e7d77f1de
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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