Hydrochloric Acid → HCID 86739942, compound

HRID 615859Notes

Reaction equation

HRID 615859 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N:7]([C@H:10]1[C@@H:13]([CH2:14][O:15][CH2:16][C:17]([O:19]C)=[O:18])[NH:12][C:11]1=[O:21])=[N+:8]=[N-:9].Cl>O.O1CCCC1>[N:7]([C@H:10]1[C@@H:13]([CH2:14][O:15][CH2:16][C:17]([OH:19])=[O:18])[NH:12][C:11]1=[O:21])=[N+:8]=[N-:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 86739941HCID 86739941, compound

Product 1

HCID 86739942HCID 86739942, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of potassium carbonate (7.335 g, 53.08 mmole) in water (80 ml) was cooled to 0° C. and deoxygenated with argon. A solution of (±)-(cis)-[(3-azido-2-oxo-4-azetidinyl)methoxy]acetic acid, methyl ester (2.261 g, 10.62 mmole) in tetrahydrofuran (60 ml) was added and the mixture stirred at 0° C. for five minutes and then at room temperature for 5.5 hours. The reaction was cooled and acidified with 6N hydrochloric acid to pH 7. The tetrahydrofuran was mostly removed in vacuo, and the aqueous residue (pH ca. 8) was extracted with ethyl acetate. The aqueous layer was cooled to 0° C., acidified with 6N hydrochloric acid to pH 2, saturated with sodium chloride, and extracted with ethyl acetate (fifteen 80 ml portions). The organic extracts were dried (sodium sulfate), filtered, and concentrated in vacuo. The yield of crude acid was 1.503 g.

Workup

  1. customdeoxygenated with argon
  2. waitat room temperature for 5.5 hours
  3. temperatureThe reaction was cooled
  4. customThe tetrahydrofuran was mostly removed in vacuo
  5. extractionthe aqueous residue (pH ca. 8) was extracted with ethyl acetate
  6. temperatureThe aqueous layer was cooled to 0° C.
  7. extractionextracted with ethyl acetate (fifteen 80 ml portions)
  8. dry with materialThe organic extracts were dried (sodium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4989e22450554852995a79113857942e
Source dataset
uspto-grants-1985_02
Patent number
US04501697

Reaction notes

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