Water → HCID 54048591, compound

HRID 373347Notes

Reaction equation

HRID 373347 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:51])[CH2:43][O:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C(N(CC)CC)C.C(#N)C.O>ClCCl>[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:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:18])[C:14](=[O:40])[C@H:13]1[NH:41][C:42](=[O:51])[CH2:43][O:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 6342AcetonitrileHCID 8471TriethylamineHCID 54371321HCID 54371321, compound

Product 1

HCID 54048591HCID 54048591, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Embodiment a: To a solution of 200 mg (0.261 mmol) of diphenylmethyl 2-[(3R, 4R)-4-[(benzothiazol-2yl)dithio]-3-phenoxyacetamido-2-oxo-azetidin-1-yl]3-fluorosulfonyloxy-2-butenoate (XXd) in 2.0 mL of dry dichloromethane at room temperature was added, dropwise, 38.26 μL (0.274 mmol) of triethylamine. The solution was stirred at ambient temperature for 25 min. HPLC indicated disappearance of the starting material and formation of the product (retention time=4.74 min, 2.0 mL/min, 70% acetonitrile: 30% water, reversed phase C-18 column). The resultant solution was poured into water. The organic layer was separated and further washed with brine (10 mL) and 5% HCl solution (10 mL). It was subsequently dried (magnesium sulfate) and concentrated to give 139.09 mg (81%) of the title product as a light brown foam, which was further purified by recrystallization from isopropanol.

Workup

  1. customThe organic layer was separated
  2. washfurther washed with brine (10 mL) and 5% HCl solution (10 mL)
  3. dry with materialIt was subsequently dried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7a8af8367f304666a4868468000f251c
Source dataset
uspto-grants-1992_11
Patent number
US05162521

Reaction notes

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