Pyridine → HCID 70178435, compound

HRID 2229498Notes

Reaction equation

HRID 2229498 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C@@H:5]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)[CH3:2].[N:23]1[CH:28]=CC=CC=1.C[S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:22])[C@@H:5]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][S:30]([CH2:28][NH2:23])(=[O:32])=[O:31])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 10638537Ethyl 4-amino-N-(tert-butoxycarbonyl)-L-phenylalaninate

Product 1

HCID 70178435HCID 70178435, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(S)-Ethyl-2-tert-butyloxycarbonylamino-3-(4-aminophenyl)propionate (0.103 g, 0.33 mmol) was dissolved in CH2Cl2 (1 mL) in a two-necked flask fitted with a thermometer and nitrogen line. The flask was cooled to 0° C. and pyridine (1.1 eq, 0.36 mmol, 0.030 mL) was added via syringe. Methanesulfonyl chloride (1.1 eq, 0.36 mmol, 0.028 mL) was then added dropwise at such a rate as to maintain the temperature <10° C. After addition was complete, the ice bath was removed and the bright yellow solution was allowed to warm to room temperature, turning bright orange and then pink in color as it stirred over the next two hours. The solution was poured into 1 M aqueous CuSO4 and the organic portion was separated. It was washed once again with aqueous CuSO4, then dried over MgSO4, filtered, and concentrated to a colorless oil (0.11 g, 84%).

Workup

  1. customfitted with a thermometer and nitrogen line
  2. temperatureto maintain the temperature <10° C
  3. additionAfter addition
  4. customthe ice bath was removed
  5. temperatureto warm to room temperature
  6. additionThe solution was poured into 1 M aqueous CuSO4
  7. customthe organic portion was separated
  8. washIt was washed once again with aqueous CuSO4
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated to a colorless oil (0.11 g, 84%)

Sources & evidence

ORD record
ord-a55cb7e55c3145bab6a7bf639f449203
Source dataset
uspto-grants-2002_07
Patent number
US06420424B1

Reaction notes

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