Methanol → HCID 54043428, compound

HRID 620218Notes

Reaction equation

HRID 620218 reaction equation
[CH3:1][O:2][C:3]([O:19][CH3:20])([O:5][C:6]([NH:8][C@H:9]([C:16]([OH:18])=[O:17])[CH2:10][C:11]1[N:15]=[CH:14][NH:13][CH:12]=1)=[O:7])[CH3:4].C(=O)([O-])[O-].[Na+].[Na+].[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.CO>O>[CH3:20][O:19][C:3]([O:2][CH3:1])([O:5][C:6]([NH:8][C@H:9]([C:16]([OH:18])=[O:17])[CH2:10][C:11]1[N:15]=[CH:14][N:13]([S:33]([C:30]2[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=2)(=[O:35])=[O:34])[CH:12]=1)=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 178496338HCID 178496338, compound

Product 1

HCID 54043428HCID 54043428, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-[(1,1-Dimethoxyethoxy)carbonyl]-L-histidine (12.7 g, 50 mmol) was dissolved in a solution of sodium carbonate (10.6 g, 100 mmol) in 150 ml water and cooled to 10°. p-Toluenesulfonylchloride (12.8 g, 67 mmol) was added in very small portions over a period of 30 minutes while maintaining vigorous stirring and controlling the temperature between 10°-15°. After the addition was complete, the reaction mixture was warmed to room temperature and stirring continued for an additional 4 hours. The reaction mixture was extracted twice with ethyl ether (75 ml) and the organic portions were discarded. The aqueous layer was acidified with 1N hydrochloric acid, extracted twice with ethyl acetate (150 ml) and the combined organic extracts were dried and concentrated to give an oily residue. Crystallization from ethyl acetate afforded 9.42 grams of the title A compound. m.p.=120°, [α]D =15.3° (c=1.66, CH3OH).

Workup

  1. temperaturecooled to 10°
  2. temperaturewhile maintaining vigorous
  3. custombetween 10°-15°
  4. additionAfter the addition
  5. stirringstirring
  6. extractionThe reaction mixture was extracted twice with ethyl ether (75 ml)
  7. extractionextracted twice with ethyl acetate (150 ml)
  8. customthe combined organic extracts were dried
  9. concentrationconcentrated
  10. customto give an oily residue
  11. customCrystallization from ethyl acetate
  12. customafforded 9.42 grams of the title A compound

Sources & evidence

ORD record
ord-96021182bed646dea2b39a495626a022
Source dataset
uspto-grants-1989_04
Patent number
US04820691

Reaction notes

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