Water → HCID 15376563, compound

HRID 2187501Notes

Reaction equation

HRID 2187501 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([S:14]([NH:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])=[O:15])[CH:5]=1.C(N(CC)CC)C.Cl[C:30]([O:32][CH3:33])=[O:31].O>ClCCl>[C:18]([NH:17][S:14]([C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][NH:1][C:30]([O:32][CH3:33])=[O:31])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])(=[O:16])=[O:15])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 15376564HCID 15376564, compound

Product 1

HCID 15376563HCID 15376563, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.45 g (4.6 mmol) of methyl 4-(2-aminoethyl)-2-tert-butylaminosulfonylbenzoate and 0.71 ml (5.1 mmol) of triethylamine in 10 ml of dichloromethane was added dropwise to an ice-cooled solution of 1.31 g (13.8 mmol) of methyl chloroformate in 20 ml of dichloromethane. After 2 h at room temperature, water was added, the phases were separated, and the aqueous phase was re-extracted twice with dichloromethane. The combined organic extracts were washed with water, dried over Na2SO4 and concentrated in vacuo. This gave 1.4 g (81%) of methyl 2-tert-butylaminosulfonyl-4-[2-(methoxycarbonylamino)ethyl]benzoate as a viscous oil.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was re-extracted twice with dichloromethane
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a1ac13b7cceb4ff896ec0e541e6f088c
Source dataset
uspto-grants-2002_06
Patent number
US06410483B1

Reaction notes

Loading…