Water → Benzyl[1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]carbamate

HRID 510963Notes

Reaction equation

HRID 510963 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[Br:12][C:13]1[C:14]([O:31][CH3:32])=[C:15]([CH:21]([NH:23]C(=O)OC(C)(C)C)[CH3:22])[CH:16]=[C:17]([Cl:20])[C:18]=1[CH3:19].C(=O)([O-])[O-].[Na+].[Na+].O>C(Cl)Cl.CCOC(C)=O>[Br:12][C:13]1[C:14]([O:31][CH3:32])=[C:15]([CH:21]([NH:23][C:2](=[O:3])[O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:22])[CH:16]=[C:17]([Cl:20])[C:18]=1[CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 88543336Tert-butyl[1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]carbamate

Product 1

HCID 123610481Benzyl[1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]carbamateYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl chloroformate (0.41 mL, 2.8 mmol) was added to a mixture of 1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanamine hydrochloride (0.50 g, 1.6 mmol, made from Example 113, step 1, chiral intermediate), and sodium carbonate (670 mg, 6.3 mmol) in methylene chloride (5 mL)/water (1 mL) at 0° C. The reaction was stirred at room temperature for 4 hours. The mixture was diluted with EtOAc, washed with water, brine, dried over Na2SO4, filtered and concentrated. The resultant residue was purified by chromatography eluting with 0 to 20% EtOAc in hexanes to provide the desired product (0.5 g, 76%). LCMS calculated for C18H19BrClNO3Na (M+Na)+: m/z=434.0. found: 434.1.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resultant residue was purified by chromatography
  6. washeluting with 0 to 20% EtOAc in hexanes

Sources & evidence

ORD record
ord-b0256eca61414186a4fa72ea6be78f6c
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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