Phosphorus oxychloride → Benzyl 5-(2-(4-bromo-2,6-dimethylphenoxy)acetamido)-2-(ethylsulfonyl)benzylcarbamate

HRID 735708Notes

Reaction equation

HRID 735708 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]([CH3:13])[C:5]([O:6][CH2:7][C:8]([OH:10])=O)=[C:4]([CH3:14])[CH:3]=1.[NH2:15][C:16]1[CH:17]=[CH:18][C:19]([S:34]([CH2:37][CH3:38])(=[O:36])=[O:35])=[C:20]([CH:33]=1)[CH2:21][NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([O:6][CH2:7][C:8]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([S:34]([CH2:37][CH3:38])(=[O:36])=[O:35])=[C:20]([CH:33]=2)[CH2:21][NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:10])=[C:11]([CH3:13])[CH:12]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 7248362-(4-Bromo-2,6-dimethylphenoxy)acetic acidHCID 57842737HCID 57842737, compound

Product 1

HCID 57842885Benzyl 5-(2-(4-bromo-2,6-dimethylphenoxy)acetamido)-2-(ethylsulfonyl)benzylcarbamateYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 79A (100 mg, 0.386 mmol) and 28A (148 mg, 0.386 mmol) in 2 mL pyridine at −15° C., was added POCl3 (0.040 mL, 0.425 mmol), dropwise. The mixture was stirred at this temperature for 20 min, then was quenched with water. The mixture was diluted with EtOAc, washed with water (2×), 1N HCl, water, sat. NaHCO3 and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography to afford 222 mg (98%) of 79B as a colorless oil. MS (ESI) m/z 589.2 (M+H)+.

Workup

  1. customwas quenched with water
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with water (2×), 1N HCl, water, sat. NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-0b7170529d054cb483a301c0922813a2
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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