Di-tert-butyl dicarbonate → HCID 58362497, compound

HRID 2361480Notes

Reaction equation

HRID 2361480 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH3:27])[C:20](=O)[O:21]C(C)(C)C)=[C:15]([N+:28]([O-:30])=[O:29])[CH:14]=1)[CH:7]=[CH:6]2.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>C1COCC1.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH3:27])[CH:20]=[O:21])=[C:15]([N+:28]([O-:30])=[O:29])[CH:14]=1)[CH:7]=[CH:6]2

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 58362452HCID 58362452, compound

Product 1

HCID 58362497HCID 58362497, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

tert-Butyl 4-(6-methoxyquinolin-2-yl)-2-nitrophenyl(methyl)carbamate AS-5332-46: To a solution AS-5332-42 (0.030 g, 0.186 mmol) in THF (3.0 mL) was added Boc anhydride (0.063 g, 0.0.291 mmol) and DMAP (0.012 g, 0.097 mmol). The resulting reaction mixture was heated at 100° C. for 30 min. The volatiles were removed in vacuo and residue was purified on a Combiflash purification system (silica gel, 0-7% EtOAc:DCM) to afford AS-5332-43 as a off white solid (0.040 g, 100%). 1H-NMR (400 MHz, CDCl3) δ: 8.69 (d, J=2.0 Hz, 1H), 8.40 (d, J=8.0 Hz, 1H), 8.16 (d, J=8.8 Hz, 1H), 8.07 (d, J=9.2 Hz, 1H), 7.85 (d, J=8.8 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 7.41 (dd, J=9.2, 2.8 1H), 7.10 (d, J=2.8 Hz, 1H), 3.95 (s, 3H), 3.34 (s, 3H), 1.32 (s, 9H); MS (ESI): 410.1 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. customThe volatiles were removed in vacuo and residue
  3. customwas purified on a Combiflash purification system (silica gel, 0-7% EtOAc:DCM)

Sources & evidence

ORD record
ord-e7cf7b097d5e44ff9a0e32f6ccb77c03
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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