Sodium Hydroxide → 3,5-Dichlorobenzyl 2-(2-((tert-butoxycarbonyl)amino)ethyl)morpholine-4-carboxylate

HRID 1480380Notes

Reaction equation

HRID 1480380 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH2:9][CH:10]1[O:15][CH2:14][CH2:13][NH:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[C:22](Cl)(=[O:33])[O:23][CH2:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=1.[OH-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][CH2:8][CH2:9][CH:10]1[O:15][CH2:14][CH2:13][N:12]([C:22]([O:23][CH2:24][C:25]2[CH:26]=[C:27]([Cl:32])[CH:28]=[C:29]([Cl:31])[CH:30]=2)=[O:33])[CH2:11]1)=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 133055323,5-Dichlorobenzyl ChloroformateHCID 25219056tert-Butyl (2-morpholin-2-ylethyl)carbamate

Product 1

HCID 867226343,5-Dichlorobenzyl 2-(2-((tert-butoxycarbonyl)amino)ethyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture comprising of t-butyl(2-morpholin-2-ylethyl)carbamate (3 g, 13.03 mmol) in DCM (100 ml), was added saturated aqueous sodium bicarbonate solution (100 ml, 13.03 mmol), followed by 3,5-dichlorobenzyl carbonochloridate (3.43 g, 14.33 mmol). The biphasic mixture was stirred at room temperature for 2 hours. The resulting mixture was treated with 2M NaOH solution (50 ml). The reaction mixture was separated and the organic portion was dried over MgSO4 and concentrated under reduced pressure to afford the title compound.

Workup

  1. customThe reaction mixture was separated
  2. dry with materialthe organic portion was dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fda5ac0bfe854e7687b6dcfb80d6a62d
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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