Cesium carbonate → HCID 69519781, compound

HRID 1294695Notes

Reaction equation

HRID 1294695 reaction equation
I[C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:21]=[CH:20][C:10]([O:11][CH:12]3[CH:17]4[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]4)[CH2:13]3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])[NH:25][NH2:26].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[C:29]([O:28][C:24]([N:25]([C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:21]=[CH:20][C:10]([O:11][CH:12]3[CH:17]4[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]4)[CH2:13]3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1)[NH2:26])=[O:27])([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 70091tert-Butyl carbazateHCID 11384641HCID 11384641, compound

Product 1

HCID 69519781HCID 69519781, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 38A (420 mg, 1.0 mmol) was coupled with tert-butyl carbazate (Aldrich, 158 mg, 1.2 mmol) under the catalysis of Cul (Strem Chemicals, 9.5 mg, 0.05 mmol) with Cs2CO3 (Strem Chemicals, 489 mg, 1.4 mmol) in DMF (anhydrous, Aldrich, 5 mL) at 80° C. overnight. The mixture was diluted with EtOAc (50 mL) and washed with water (2×10 mL). The organic solution was concentrated and the title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.20) as an oil (190 mg, yield, 45%). 1H NMR (MeOH-d4, 300 MHz) δ 1.46 (s, 9H), 1.76–2.16 (m, 3H), 2.20–2.39 (m, 1H), 2.41–2.54 (m, 1H), 3.16–3.47 (m, 5H), 3.66–3.86 (m, 1H), 4.70–4.84 (m, 1H), 6.77–6.93 (m, 2H), 6.94–7.04 (m, 4H), 7.25–7.48 (m, 2H) ppm. MS (DCl/NH3) m/z 426 (M+H)+.

Workup

  1. washwashed with water (2×10 mL)
  2. concentrationThe organic solution was concentrated
  3. customthe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.20) as an oil (190 mg, yield, 45%)

Sources & evidence

ORD record
ord-886a964f38eb4179b092b9b34ff5ed53
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

Loading…