Cesium carbonate → HCID 131731962, compound

HRID 538997Notes

Reaction equation

HRID 538997 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:13]=[N:14][N:15]4[CH:20]=[CH:19][C:18]([N:21]5[C@@H:25]([CH:26]([CH3:28])[CH3:27])[CH2:24][O:23][C:22]5=[O:29])=[N:17][C:16]=34)=[CH:8][CH:7]=2)=[N:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[P:36]([O:48][CH2:49]Cl)([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>CN(C=O)C>[P:36]([O:48][CH2:49][N:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[CH:13]=[N:14][N:15]4[CH:20]=[CH:19][C:18]([N:21]5[C@@H:25]([CH:26]([CH3:27])[CH3:28])[CH2:24][O:23][C:22]5=[O:29])=[N:17][C:16]=34)=[CH:10][CH:11]=2)=[N:2]1)([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:37]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11701630Di-tert-butyl (chloromethyl) phosphateHCID 178448158HCID 178448158, compound

Product 1

HCID 131731962HCID 131731962, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of (S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one (1.72 g, 4.42 mmol), Cs2CO3 (1.58 g, 4.86 mmol) and DMF (40 mL) was added di-tert-butyl chloromethyl phosphate (1.54 g, 5.96 mmol). The reaction mixture was heated at 80° C. for 2 hours. After cooling, the reaction mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water and brine, dried and concentrated. The residue was purified by column chromatography (1:1 to 4:1 EtOAc:hexane) to give (S)-di-tert-butyl (3-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1H-1,2,4-triazol-1-yl)methyl phosphate (0.42 g, 16%). LCMS (APCI+) m/z 612 [M+H]+.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (1:1 to 4:1 EtOAc:hexane)

Sources & evidence

ORD record
ord-00e8c68b9d274142a30664fced219ec3
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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