Sodium Chloride → HCID 10439229, compound

HRID 258431Notes

Reaction equation

HRID 258431 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][S:11][C@H:12]1[N:15]([C:16](=[C:33](OS(F)(=O)=O)[CH3:34])[C:17]([O:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C:14](=[O:40])[C@H:13]1[NH:41][C:42](=[O:50])[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(N(CC)CC)C.[Na+].[Cl-]>C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][S:11][C@H:12]1[N:15]([C:16](=[C:33]=[CH2:34])[C:17]([O:19][CH:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:18])[C:14](=[O:40])[C@H:13]1[NH:41][C:42](=[O:50])[CH2:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 54201921HCID 54201921, compound

Product 1

HCID 10439229HCID 10439229, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a stream of dry nitrogen, the flask was charged with 500 mg (0.65 mmol) of diphenylmethyl 2-[(3R, 4R)-4-[(benzothiazol-2-yl)dithio]-3-phenylacetamido-2-oxo-azetidin-1-yl]-3-fluorosulfonyloxy-2-butenoate (XVf) and 5.0 mL of dry THF. After stirring the solution for 15 min at 0°-5° C., 92.0 μL (0.65 mmol) of triethylamine was added dropwise. Stirring at 0°-5° C. under a blanket of dry nitrogen was continued for 2 h. The solution was diluted with THF (10 mL) and poured into an aqueous saturated NaCl solution (30 mL). The phases were separated and the organic phase was dried 15 min over anhydrous MgSO4, filtered and concentrated to a small volume (ca. 6 mL). The solution was added dropwise into 36 mL of hexanes with vigorous stirring. After 30 min, the solid was collected by suction filtration and dried in vacuo for 3 h at 22° C. to yield 387 mg (92%) of the title product as a beige powder.

Workup

  1. stirringStirring at 0°-5° C. under a blanket of dry nitrogen
  2. waitwas continued for 2 h
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried 15 min over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a small volume (ca. 6 mL)
  7. additionThe solution was added dropwise into 36 mL of hexanes with vigorous stirring
  8. waitAfter 30 min
  9. filtrationthe solid was collected by suction filtration
  10. customdried in vacuo for 3 h at 22° C.

Sources & evidence

ORD record
ord-bbfbf8c8f1d34ac1a0958c86609186b9
Source dataset
uspto-grants-1993_11
Patent number
US05266691

Reaction notes

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