Hydrochloric Acid → HCID 11790499, compound

HRID 2118548Notes

Reaction equation

HRID 2118548 reaction equation
S(N[C@H](C([O:16][C:17]1[C:26]2[O:25][CH2:24][C@H:23]([O:27][N+:28]([O-:30])=[O:29])[CH2:22][C:21]=2[CH:20]=[CH:19][CH:18]=1)=O)CC1C=CC=CC=1)(C)(=O)=O.CO.[OH-].[Na+].Cl>O1CCCC1>[O:27]([C@@H:23]1[CH2:22][C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:16])[C:26]=2[O:25][CH2:24]1)[N+:28]([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 13767641HCID 13767641, compound

Product 1

HCID 11790499HCID 11790499, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

21.6 g of the ester obtained in (A) was dissolved in 200 ml of tetrahydrofuran, and at room temperature, 100 ml of methanol and then 40 ml of a 10% aqueous solution of sodium hydroxide were added. The mixture was stirred for 1 hour. The reaction mixture was adjusted to a pH of about 4 with cold hydrochloric acid, and concentrated. To the residue were added 300 ml of chloroform and dilute hydrochloric acid. The aqueous layer was adjusted to pH 2, and the chloroform layer was separated. The chloroform layer was washed with an aqueous solution of sodium hydrogen carbonate and also with water, and the solvent was evaporated. Recrystallization of the residue from ethyl acetate-hexane gave 9.2 g (yield 38.0%) of the desired product as colorless prisms having a melting point of 129.0° to 130.5° C.

Workup

  1. concentrationconcentrated
  2. additionTo the residue were added 300 ml of chloroform and dilute hydrochloric acid
  3. customthe chloroform layer was separated
  4. washThe chloroform layer was washed with an aqueous solution of sodium hydrogen carbonate and also with water
  5. customthe solvent was evaporated
  6. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a8542cd8c6374e46a5431a2467b6ea6c
Source dataset
uspto-grants-1987_07
Patent number
US04678803

Reaction notes

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