Cesium carbonate → HCID 86618166, compound

HRID 2246608Notes

Reaction equation

HRID 2246608 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:33][CH2:34]SC)[C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][C@@H:19]([O:22][CH3:23])[CH2:18][C@H:17]1[CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+]>IC.CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:33][CH2:34][N:15]([C@H:16]2[CH2:21][CH2:20][C@@H:19]([O:22][CH3:23])[CH2:18][C@H:17]2[CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:13]1=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 10796Cesium carbonateHCID 86618164HCID 86618164, compound

Product 1

HCID 86618166HCID 86618166, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6328Methyl iodideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A sample of the product from Step 7 was dissolved in iodomethane (30 ml) and stirred at room temperature for two days. The reaction mixture was evaporated and dried in vacuo. The residue was dissolved in CH2Cl2 and evaporated. The process was repeated four more times. The resulting residue was dried in vacuo to yield a yellow foamy solid which was then taken in DMF (20 ml) and treated with Cs2CO3 (6.36 g, 19.52 mmol). The reaction mixture was stirred at room temperature overnight. It was diluted with EtOAc and washed with water (2×). The combined aqueous layer was extracted with EtOAc (2×). The combined organic layer was then washed with brine and dried over anhydrous MgSO4. The solution was then concentrated and chromatographed to yield tert-butyl ((1S,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-methoxycyclohexyl)methylcarbamate as a white foamy solid. LC/MS found [M+H]+=476.4

Workup

  1. customThe reaction mixture was evaporated
  2. customdried in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. customevaporated
  5. customThe resulting residue was dried in vacuo
  6. customto yield a yellow foamy solid which
  7. stirringThe reaction mixture was stirred at room temperature overnight
  8. washwashed with water (2×)
  9. extractionThe combined aqueous layer was extracted with EtOAc (2×)
  10. washThe combined organic layer was then washed with brine
  11. dry with materialdried over anhydrous MgSO4
  12. concentrationThe solution was then concentrated
  13. customchromatographed

Sources & evidence

ORD record
ord-77cce9f73d2543409a24acbe2df942d9
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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