Hydrochloric Acid → HCID 56979190, compound

HRID 21712Notes

Reaction equation

HRID 21712 reaction equation
C(OC([O:11][C@@H:12]([C@@H:14]1[C@@H:17]([C@H:18]([C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[S:21])[CH3:19])[N:16]([CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])[C:15]1=[O:36])[CH3:13])=O)C1C=CC=CC=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+].Cl>ClCCCl.C(OCC)(=O)C>[OH:11][C@@H:12]([C@@H:14]1[C@@H:17]([C@H:18]([C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[S:21])[CH3:19])[N:16]([CH2:28][C:29]([OH:31])=[O:30])[C:15]1=[O:36])[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 57040172HCID 57040172, compound

Product 1

HCID 56979190HCID 56979190, compoundYield 194.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3S,4S)-3-[(1R)-1-benzyloxycarbonyloxyethyl]-4-[(1R)-1-phenylthiocarbonylethyl]-1-t-butoxycarbonylmethylazetidin-2-one (8.5 g) in 1,2-dichloroethane (185 ml), there was dropwise added a solution of boron tribromide (26.4 g) in 1,2-dichloroethane (100 ml) at -10° C. for 20 minutes, followed by stirring at the same temperature for 1 hour. Sodium bicarbonate (40 g) and ice-water (600 g) were added thereto while stirring, and the resultant mixture was diluted with ethyl acetate (200 ml). The aqueous layer was acidified with 2N hydrochloric acid (200 ml), extracted with ethyl acetate and combined with the organic layer. The combined organic layer was washed with brine (200 ml×3), dried over magnesium sulfate and evaporated in vacuo to give (3S,4S)-3-[(1R)-1-hydroxyethyl]-4-[(1R)-1-phenylthiocarbonylethyl]-1-carboxymethylazetidin-2-one (10.4 g, 87.9%.).,

Workup

  1. stirringwhile stirring
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine (200 ml×3)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-9a352419d48e439da235f9c189e0d847
Source dataset
uspto-grants-1995_06
Patent number
US05424422

Reaction notes

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