Cesium carbonate → HCID 69271800, compound

HRID 2219033Notes

Reaction equation

HRID 2219033 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][CH:8]1[C:14](=[O:15])[N:13]([CH2:16][CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12]2[CH:26]=[CH:27][CH:28]=[CH:29][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:31](=[O:34])([O-])[O-:32].[Cs+].[Cs+].FC(F)(F)S(O[CH2:43][C:44]([F:47])([F:46])[F:45])(=O)=O>CN(C)C=O>[F:45][C:44]([F:47])([F:46])[CH2:43][O:32][C:31]([N:10]1[CH2:9][C@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:30])[C:14](=[O:15])[N:13]([CH2:16][CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12]2[CH:26]=[CH:27][CH:28]=[CH:29][C:11]1=2)=[O:34]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 59718671HCID 59718671, compound

Product 1

HCID 69271800HCID 69271800, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 301 mg of [(RS)-1-(2-benzyloxy-ethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester in 6 ml of N,N-dimethylformamide was treated with 477 mg of cesium carbonate, 350 mg of 2,2,2-trifluoroethyl trifluoromethanesulphonate, and about 300 mg of solid carbondioxide. The reaction mixture was stirred in a sealed tube at 60° C. for 18 hours. For the working-up, the solvent was evaporated under reduced pressure, and the residue was distributed between 10 ml of a saturated sodium hydrogencarbonate solution and 30 ml of ethyl acetate. The aqueous layer was separated and extracted twice with 30 ml of ethyl acetate. The combined organic layers were dried over sodium sulphate and evaporated under reduced pressure. For purification, the light brown oil was separated on silica gel using a gradient of heptane/ethyl acetate=100/0 to 60/20 as the eluent. There were obtained 325 mg (83% of theory) of the title compound as a white foam [MS (m/e): 538 (M+H)+].

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe aqueous layer was separated
  3. extractionextracted twice with 30 ml of ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. customevaporated under reduced pressure
  6. customFor purification
  7. customthe light brown oil was separated on silica gel using a gradient of heptane/ethyl acetate=100/0 to 60/20 as the eluent

Sources & evidence

ORD record
ord-f37c39f84b544e19b1d7e95c11980166
Source dataset
uspto-grants-2008_08
Patent number
US07414049B2

Reaction notes

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