Hydrochloric Acid → HCID 56979190, compound

HRID 1033459Notes

Reaction equation

HRID 1033459 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-86ea4f96d1b44a198d2b35125666b5c5
Source dataset
uspto-grants-1994_05
Patent number
US05310897

Reaction notes

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