Cesium carbonate → HCID 57986908, compound

HRID 871942Notes

Reaction equation

HRID 871942 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[S:13][CH:14]=[C:15]([CH2:17]Cl)[N:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:19]1([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[CH:23]=[N:22][N:21]=[N:20]1.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[S:13][CH:14]=[C:15]([CH2:17][O:30][C:27]3[CH:28]=[CH:29][C:24]([N:19]4[CH:23]=[N:22][N:21]=[N:20]4)=[CH:25][CH:26]=3)[N:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 5429104-(1H-1,2,3,4-tetrazol-1-yl)phenolHCID 57423799HCID 57423799, compound

Product 1

HCID 57986908HCID 57986908, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(4-chloromethyl-thiazol-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (From Step 1) (386 mg, 1.34 mmol), 4-tetrazol-1-yl-phenol (217 mg, 1.34 mmol), Cs2CO3 (655 mg, 2.01 mmol) and KI (22 mg, 0.13 mmol) in acetonitrile (5 mL) was heated under reflux for 4 hours. After cooling, the solid was filtered through a pad of celite. The filtrate was concentrated in vacuo. The residue was purified on silica gel (EtOAc-hexanes, 1:1) to afford the desired product. 1H NMR (CDCl3): δ 8.92 (1H, s), 7.61 (2H, d), 7.32 (1H, s), 7.19 (2H, d), 5.25 (2H, s), 4.39 (2H, m), 4.18 (2H, m), 4.14 (1H, m), 1.46 (9H, s).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling
  4. filtrationthe solid was filtered through a pad of celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified on silica gel (EtOAc-hexanes, 1:1)

Sources & evidence

ORD record
ord-7b95b85f4d094741bb82a0bb2f297207
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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