Hydrochloric Acid → HCID 20139866, compound

HRID 1252514Notes

Reaction equation

HRID 1252514 reaction equation
[CH3:1][CH:2]([CH3:17])[CH2:3][CH:4]1[NH:9][C:8](=[O:10])[CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6][CH2:5]1.Cl.[OH-:19].[Na+].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>O>[CH3:1][CH:2]([CH3:17])[CH2:3][CH:4]([NH:9][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[CH2:5][O:6][CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([OH:19])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 20139873HCID 20139873, compound

Product 1

HCID 20139866HCID 20139866, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(2-Methylpropyl)-2-phenyl-3-morpholinone (center phenyl is R, S, other center is S), 0.95 g (0.0041 mole), was suspended in a solution of 50 ml of concentrated hydrochloric acid and 50 ml of water, heated for one hour on a steam bath, cooled to room temperature, and extracted with 100 ml of dichloromethane. The aqueous layer was separated and the pH adjusted with sodium hydroxide to pH 10.5 and 0.84 g (0.0049 mole) of benzyl chloroformate was added dropwise while the pH was maintained at 10.5 with sodium hydroxide. After addition was complete the mixture was extracted with 100 ml of diethylether, the aqueous layer was separated and the pH adjusted to 3 by the addition of a 10% aqueous solution of hydrochloric acid. The mixture was extracted with 200 ml of dichloromethane. The dichloromethane layer was separated, dried over sodium sulfate, evaporated in vacuo and the residue purified by chromatography using silica gel and eluting with 1 l of dichloromethane-methanol (95:5) to give α-[[4-methyl-2[[(phenylmethoxy)carbonyl]amino]pentyl]oxy]benzeneacetic acid (α-carbon is R, S, other stereo site is S), 1.1 g; [α]D25 =-78.9° (C, 0.56, methanol).

Workup

  1. temperatureheated for one hour on a steam bath
  2. extractionextracted with 100 ml of dichloromethane
  3. customThe aqueous layer was separated
  4. additionwas added dropwise while the pH
  5. additionAfter addition
  6. extractionwas extracted with 100 ml of diethylether
  7. customthe aqueous layer was separated
  8. additionthe pH adjusted to 3 by the addition of a 10% aqueous solution of hydrochloric acid
  9. extractionThe mixture was extracted with 200 ml of dichloromethane
  10. customThe dichloromethane layer was separated
  11. dry with materialdried over sodium sulfate
  12. customevaporated in vacuo
  13. customthe residue purified by chromatography
  14. washeluting with 1 l of dichloromethane-methanol (95:5)

Sources & evidence

ORD record
ord-dc8bf845364b4457b6acab720c4ced4d
Source dataset
uspto-grants-1988_05
Patent number
US04743585

Reaction notes

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