Cesium carbonate → 2-(4-Chloro-3-methylphenyl)-2-oxoethyl (3-{[(benzyloxy)carbonyl]amino}oxetan-3-yl)acetate

HRID 1523283Notes

Reaction equation

HRID 1523283 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([CH2:16][C:17]([OH:19])=[O:18])[CH2:15][O:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([CH3:31])[CH:25]=1)=[O:23].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:1]([O:8][C:9]([NH:11][C:12]1([CH2:16][C:17]([O:19][CH2:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([CH3:31])[CH:25]=2)=[O:23])=[O:18])[CH2:13][O:14][CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 5928022-Bromo-1-(4-chloro-3-methylphenyl)ethanoneHCID 895254372-(3-{[(Benzyloxy)carbonyl]amino}oxetan-3-yl)acetic acid

Product 1

HCID 1234125342-(4-Chloro-3-methylphenyl)-2-oxoethyl (3-{[(benzyloxy)carbonyl]amino}oxetan-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3-{[(Benzyloxy)carbonyl]amino}oxetan-3-yl)acetic acid (Preparation 25, 0.3 g, 1.13 mmol), 2-bromo-1-(4-chloro-3-methylphenyl)ethanone (0.294 g, 1.19 mmol) and cesium carbonate (0.553 g, 1.70 mmol) were stirred in acetonitrile (10 mL) at room temperature for 2 hours. The reaction was concentrated in vacuo and partitioned between ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated in vacuo to afford the title compound which was used without purification in the next step.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee10378556ba43c5bb6d23beaf0895c3
Source dataset
uspto-grants-2015_07
Patent number
US09079878B2

Reaction notes

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