Ethyl Acetate → HCID 86606019, compound

HRID 130512Notes

Reaction equation

HRID 130512 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].[CH2:12]([O:14][C:15]([C@:17]1([F:37])[C@@H:22]2[C@H:18]1[CH2:19][C@@H:20]([OH:36])[C@@:21]2([N:33]=[N+:34]=[N-:35])[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])=[O:16])[CH3:13].C(OCC)(=O)C>N1C=CC=CC=1>[CH2:12]([O:14][C:15]([C@:17]1([F:37])[C@@H:22]2[C@H:18]1[CH2:19][C@@H:20]([O:36][C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([Cl:11])=[C:2]([Cl:1])[CH:3]=1)[C@@:21]2([N:33]=[N+:34]=[N-:35])[C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24])=[O:16])[CH3:13]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 11337440HCID 11337440, compound

Product 1

HCID 86606019HCID 86606019, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

234 mg of 3,4-dichlorobenzoyl chloride was added to 202 mg of (1R,2R,3R,5R,6R)-2-azido-6-fluoro-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester dissolved in 3.7 mL of pyridine, and the mixture was stirred for 28 hours at room temperature, under a nitrogen atmosphere. After 100 mL of ethyl acetate was added to the reaction solution, this ethyl acetate solution was washed with a saturated aqueous solution of copper sulfate and with water, and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel C200, eluent: hexane-ethyl acetate=10:1), thereby yielding 298 mg of (1R,2R,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzoyloxy)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester.

Workup

  1. washthis ethyl acetate solution was washed with a saturated aqueous solution of copper sulfate and with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel: Wako gel C200, eluent: hexane-ethyl acetate=10:1)

Sources & evidence

ORD record
ord-631c4d130dde4459b172d980c66c0487
Source dataset
uspto-grants-2008_06
Patent number
US07381746B2

Reaction notes

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