Cesium carbonate → HCID 86596886, compound

HRID 1455428Notes

Reaction equation

HRID 1455428 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:38][CH2:39]SC)[C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][C@@H:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:18][C@H:17]1[CH2:30][S:31]([C:34]([CH3:37])([CH3:36])[CH3:35])(=[O:33])=[O:32])=[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.C(Cl)Cl.CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:38][CH2:39][N:15]([C@H:16]2[CH2:21][CH2:20][C@@H:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:18][C@H:17]2[CH2:30][S:31]([C:34]([CH3:37])([CH3:36])[CH3:35])(=[O:32])=[O:33])[C:13]1=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 10796Cesium carbonateHCID 86596887HCID 86596887, compound

Product 1

HCID 86596886HCID 86596886, compoundYield 96.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6328Methyl iodideSolventHCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (1R,3R,4S)-4-((S)-2-benzyloxycarbonylamino-4-(methylthio)butanamido)-3-(tert-butylsulfonylmethyl)cyclohexylcarbamate (6.2 g) was dissolved in iodomethane (60 mL) and CH2Cl2 (15 mL). The resulting solution was stirred at rt for 72 h before being concentrated in vacuo. The residue was dissolved in methylene chloride, and the resulting solution was concentrated; this was repeated to afford the salt. This material was dissolved in DMF (60 mL) and the solution was charged with Cs2CO3 (13.2 g). After 12 h, the reaction was partitioned between EtOAc and brine. The organic phase was dried (MgSO4), filtered, and concentrated to afford tert-butyl (1R,3R,4S)-4-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-3-(tert-butylsulfonylmethyl)cyclohexylcarbamate (5.5 g). MS found: (M+H)+=566.5.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride
  3. concentrationthe resulting solution was concentrated
  4. customto afford the salt
  5. waitAfter 12 h
  6. customthe reaction was partitioned between EtOAc and brine
  7. dry with materialThe organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a30b53a940224dd4a7a0f6056fe267bb
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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