Benzoyl chloride → HCID 68423856, compound

HRID 1818916Notes

Reaction equation

HRID 1818916 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 382207Tert-butyl 4-aminophenethylcarbamate

Product 1

HCID 68423856HCID 68423856, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [2-(4-amino-phenyl)-ethyl]-carbamic acid tert-butyl ester (compound 1.1; 1.0 mmol, prepared according to the procedure of Hah, J. M. et. al J. Med. Chem 46, 2003, 1661) and triethylamine (“TEA”; 3.0 equivalents) in anhydrous tetrahydrofuran (“THF”; 5.0 mL) is treated with the dropwise addition of benzoyl chloride (1.1 equivalents) at 0° C. After completion of the reaction, the mixture is partitioned between water and diethyl ether. The organic layer is separated, washed with 1.0 N HCl, saturated sodium bicarbonate, brine and dried. Purification by flash column chromatography on silica gel provides [2-(4-benzoylamino-phenyl)-ethyl]-carbamic acid tert-butyl ester (compound 1.2).

Workup

  1. custom1.0 mmol, prepared
  2. customAfter completion of the reaction
  3. customthe mixture is partitioned between water and diethyl ether
  4. customThe organic layer is separated
  5. washwashed with 1.0 N HCl, saturated sodium bicarbonate, brine
  6. customdried
  7. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-bd0071d13e894864924877b9bcb0d00a
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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