Sodium Carbonate → HCID 89862862, compound

HRID 1497030Notes

Reaction equation

HRID 1497030 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:3][CH2:2]1.C([O-])([O-])=O.[Na+].[Na+].[C:25](Cl)(=[O:29])[O:26][CH2:27][CH3:28]>C(Cl)Cl>[C:14]([O:13][C:12]([NH:11][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]([C:25]([O:26][CH2:27][CH3:28])=[O:29])[CH2:2][CH2:3]1)=[O:18])([CH3:15])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 4078484tert-Butyl 1,2,3,4-tetrahydroquinolin-4-ylcarbamate

Product 1

HCID 89862862HCID 89862862, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 1,2,3,4-tetrahydroquinolin-4-ylcarbamate (65 mg, 0.26 mmol) in DCM (1 mL) was added Na2CO3 (55.5 mg, 0.520 mmol), followed by ethyl carbonochloridate (0.028 mL, 0.29 mmol). The reaction mixture was stirred at rt for 2 h. The reaction mixture was diluted with DCM, washed with 1N HCl, dried over Na2SO4, filtered, and concentrated in vacuo to give Intermediate 38A (72 mg, 0.23 mmol, 86% yield). LCMS=1.97 min [M+Na]=342.9 (Method B).

Workup

  1. washwashed with 1N HCl
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77b507005c9b45bf98d97ac4bc75b59c
Source dataset
uspto-grants-2015_12
Patent number
US09199946B2

Reaction notes

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