Hydrochloric Acid → HCID 11139540, compound

HRID 1110457Notes

Reaction equation

HRID 1110457 reaction equation
[BH4-].[Na+].C[O:4][C:5]([C@H:7]1[NH:10][C:9](=[O:11])[C@H:8]1[NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=O.Cl.[Cl-].[Na+]>O1CCCC1.[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C>[OH:4][CH2:5][C@H:7]1[NH:10][C:9](=[O:11])[C@H:8]1[NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 12762148HCID 12762148, compound

Product 1

HCID 11139540HCID 11139540, compoundYield 68.9%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of zinc chloride (23.2 g) in anhydrous tetrahydrofuran (300 ml) at 0° C. is added sodium borohydride (13.8 g) and the mixture is allowed to warm to room temperature and is stirred overnight. To the mixture is added cis-(±)-4-(methoxycarbonyl)-3-[((phenylmethoxy)carbonyl)amino]-2-azetidinone (39.2 g) and the reaction mixture is slowly heated to 65° C. and stirred at that temperature for 2 hours. The reaction mixture is cooled to 0° C. and 6N hydrochloric acid (200 ml) is added dropwise with stirring. The mixture is poured into ethyl acetate (1 l) and the organic layer is taken. The aqueous layer is saturated with sodium chloride and re-extracted with ethyl acetate (200 ml). The combined organic layer is washed with water (200 ml) and with 200 ml of brine twice and dried over anhydrous sodium sulfate. The solvent is concentrated under reduced pressure to afford a yellow oil which is purified by column chromatography on silica gel (ethyl acetate as eluent) to obtain 24.3 g of the title product. Physical characteristics are as follows:

Workup

  1. temperaturethe reaction mixture is slowly heated to 65° C.
  2. stirringstirred at that temperature for 2 hours
  3. temperatureThe reaction mixture is cooled to 0° C.
  4. stirringwith stirring
  5. extractionre-extracted with ethyl acetate (200 ml)
  6. washThe combined organic layer is washed with water (200 ml) and with 200 ml of brine twice
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationThe solvent is concentrated under reduced pressure
  9. customto afford a yellow oil which
  10. customis purified by column chromatography on silica gel (ethyl acetate as eluent)

Sources & evidence

ORD record
ord-a581c13962c444fb8fc101aa5facc346
Source dataset
uspto-grants-1990_12
Patent number
US04975538

Reaction notes

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