Ethyl chloroformate → HCID 67125951, compound

HRID 929988Notes

Reaction equation

[CH3:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([OH:19])=O)=[N:15][CH:16]=2)[CH2:4][C:3]1([CH3:21])[CH3:20].ClC(OCC)=O.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:31][CH:30]=1>C(Cl)Cl.C1COCC1>[CH3:1][N:2]1[C:3]([CH3:20])([CH3:21])[CH2:4][CH:5]([O:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([NH:28][C:29]3[CH:30]=[CH:31][C:32]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[CH:33][CH:34]=3)=[O:19])=[N:15][CH:16]=2)[CH2:6][C:7]1([CH3:8])[CH3:9]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 5-(1,2,2,6,6-pentamethylpiperidin-4-yloxy)picolinic acid (250 mg, 0.86 mmol) in DCM/THF (6 mL, 2:1, v/v) at rt was added TEA (144 μL, 1.03 mmol) and ethyl chloroformate (82 μL, 0.86 mmol). The resulting mixture was stirred at rt for 20 min before tert-butyl 4-aminophenylcarbamate (178 mg, 0.86 mmol) was added. The resulting mixture was heated at 50° C. for 1 h. LC-MS indicated the reaction was complete. Solvents were then removed under reduced pressure and the residue was partitioned between EtOAc (30 mL) and brine (20 mL). The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to give crude tert-butyl 4-(5-(1,2,2,6,6-pentamethylpiperidin-4-yloxy)picolinamido)phenylcarbamate (500 mg) as an off-white foam. LC-MS (ESI) m/z 483 (M+H)+.

Workup

additionwas added
customSolvents were then removed under reduced pressure
customthe residue was partitioned between EtOAc (30 mL) and brine (20 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-7c5c870644fe48809c6e027065f44170
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296722B2

Reaction notes

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