Potassium Carbonate → HCID 118379430, compound

HRID 708454Notes

Reaction equation

HRID 708454 reaction equation
[NH2:1]/[C:2](=[CH:38]\[C:39](=[O:49])[CH2:40][NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])/[CH2:3][C@@H:4]1[C@H:7]([NH:8][C:9](=[O:36])/[C:10](=[N:24]\[O:25][C:26]([CH3:35])([CH3:34])[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])/[C:11]2[N:12]=[C:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[S:14][CH:15]=2)[C:6](=[O:37])[NH:5]1.Cl.NO.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:45]([O:44][C:42]([NH:41][CH2:40][C:39]1[O:49][N:1]=[C:2]([CH2:3][C@@H:4]2[C@H:7]([NH:8][C:9](=[O:36])/[C:10](=[N:24]\[O:25][C:26]([CH3:34])([CH3:35])[C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])/[C:11]3[N:12]=[C:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[S:14][CH:15]=3)[C:6](=[O:37])[NH:5]2)[CH:38]=1)=[O:43])([CH3:48])([CH3:47])[CH3:46]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 118379334HCID 118379334, compound

Product 1

HCID 118379430HCID 118379430, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 2-(((Z)-(2-(((2R,3S)-2-((Z)-2-amino-5-((tert-butoxycarbonyl)amino)-4-oxopent-2-en-1-yl)-4-oxoazetidin-3-yl)amino)-1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoethylidene)amino)oxy)-2-methylpropanoate (77 mg, 0.108 mmol)) in ethanol (0.4 mL) was added hydroxylamine hydrochloride (19 mg, 0.27 mmol) and potassium carbonate (18 mg, 0.13 mmol) and heated to 60° C. After 6 h, the reaction mixture was partially concentrated in vacuo and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (3×). Combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by column chromatography (EtOAc-Heptane, 5-90%) to afford the title compound (13 mg, 17%). LCMS: Rt=1.04 min, m/z=708.3 (M+1). Method 2m_acidic.

Workup

  1. concentrationthe reaction mixture was partially concentrated in vacuo
  2. custompartitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. washCombined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by column chromatography (EtOAc-Heptane, 5-90%)

Sources & evidence

ORD record
ord-7e9618db2ea54ea88de31ca43179bdc4
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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