Citric Acid → HCID 11536081, compound

HRID 604974Notes

Reaction equation

HRID 604974 reaction equation
C(OC([C@:6]1([CH:21]([CH3:23])[CH3:22])[C:19](=[O:20])[N:9]2[C@@H:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:11][CH2:12][C@@H:8]2[CH2:7]1)=O)C.[OH-].[Na+].C1(C)C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH:21]([C@H:6]1[C:19](=[O:20])[N:9]2[C@@H:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:11][CH2:12][C@@H:8]2[CH2:7]1)([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 1140TolueneHCID 14798Sodium HydroxideHCID 66814099HCID 66814099, compound

Product 1

HCID 11536081HCID 11536081, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 960 g of (3R,6R,7aS)-6-isopropyl-5-oxo-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazole-6-carboxylic acid ethyl ester in 8 L of tetrahydrofuran is treated with 3.33 L of a 2.0 M solution of sodium hydroxide at room temperature. The reaction mixture is stirred for 24 hours toluene (5.15 L) is added and the reaction pH adjusted to between 2-4 with a 10% solution of citric acid. The layers are separated and the aqueous layer saturated with sodium chloride. The aqueous layer is washed with 4 L of toluene and the organic layers combined and dried. The toluene solution is heated to reflux for 48 hours. Finally the solution is cooled to 70° C. and the toluene removed under a slight negative pressure to give (3R,6S,7aS)-6-isopropyl-3-phenyltetrahydro-pyrrolo[1,2-c]oxazol-5-one.

Workup

  1. additionis added
  2. customthe reaction
  3. customThe layers are separated
  4. washThe aqueous layer is washed with 4 L of toluene
  5. customdried
  6. temperatureThe toluene solution is heated
  7. temperatureto reflux for 48 hours
  8. customthe toluene removed under a slight negative pressure

Sources & evidence

ORD record
ord-511f95711fad4c7abde73aa3c2b6b9c2
Source dataset
uspto-grants-2011_03
Patent number
US07910774B2

Reaction notes

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