HCID 86695218, compound → HCID 86695223, compound

HRID 1504062Notes

Reaction equation

HRID 1504062 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:44])[CH:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[C:27]3[C:26]4[C@@H:25]([CH2:28][C@@H:29]([NH:33][C:34](=O)[O:35]CC5C=CC=CC=5)[C:30](=[O:32])[NH2:31])[CH2:24][CH2:23][C:22]=4[S:21][C:20]=3[N:19]=[CH:18][N:17]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.C(OCC)(=O)C>[O:35]=[C:34]1[NH:33][C@H:29]([CH2:28][C@H:25]2[CH2:24][CH2:23][C:22]3[S:21][C:20]4[N:19]=[CH:18][N:17]=[C:16]([O:15][CH:12]5[CH2:11][CH2:10][CH:9]([N:8]([CH3:44])[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:14][CH2:13]5)[C:27]=4[C:26]2=3)[C:30](=[O:32])[NH:31]1

Participants

4

Reactant 1

HCID 86695218HCID 86695218, compound

Product 1

HCID 86695223HCID 86695223, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of benzyl N-[(1R)-2-[(3R)-12-[(4-[[(tert-butoxy)carbonyl](methyl)amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]-1-carbamoylethyl]carbamate (80 mg, 0.15 mmol, 1.00 equiv) in 20 mL of THF was added TBAF hydrate (134 mg, 0.51 mmol, 4.00 equiv) at room temperature. The resulting solution was stirred for 4 h at 70° C. under nitrogen. After cooling down to room temperature, the resulting solution was diluted with 50 mL of ethyl acetate and washed with H2O and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10) to yield 60 mg (94%) of tert-butyl N-(4-[[(3R)-3-[[(4R)-2,5-dioxoimidazolidin-4-yl]methyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate as a white solid.

Workup

  1. temperatureAfter cooling down to room temperature
  2. washwashed with H2O and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-994e8e53489e41cf97f528b082770a95
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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