Hydrochloric Acid → HCID 54571482, compound

HRID 567945Notes

Reaction equation

HRID 567945 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([OH:20])=[O:19])[NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Si](C)(C)C.C(N(C(C)C)CC)(C)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37].Cl>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([OH:20])=[O:19])[NH:17][S:36]([CH3:35])(=[O:38])=[O:37])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 1715626epsilon-(Benzyloxycarbonyl)-L-lysine

Product 1

HCID 54571482HCID 54571482, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-N6-Benzyloxycarbonyllysine (1.5 kg) was slurried in methylene chloride (7.5 l) and chlorotrimethylsilane (1.36 l) added over 10 minutes. The mixture was heated under reflux for 30 minutes to give a solution which was cooled to 3° C. before simultaneously adding diisopropylethylamine (1.87 l) and methanesulphonyl chloride (435 ml) at such a rate as to keep the temperature below 25° C. The reaction was stirred for a further 2.5 hours then poured into 2 M aqueous hydrochloric acid solution. The layers were separated and the methylene chloride phase was washed with 2 M aqueous hydrochloric acid solution followed by water. The solvent was removed under reduced pressure and replaced with n-butyl acetate. The solution was cooled and the resulting crystalline material was collected by filtration, washed with n-butyl acetate and dried under reduced pressure to provide the title compound (1.63 kg), m.p. 83.5-84° C. [α]D25−13.4° (c=1, methanol). Found: C,50.23; H,6.40; N,7.76.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. customto give a solution which
  4. customthe temperature below 25° C
  5. customThe layers were separated
  6. washthe methylene chloride phase was washed with 2 M aqueous hydrochloric acid solution
  7. customThe solvent was removed under reduced pressure
  8. temperatureThe solution was cooled
  9. filtrationthe resulting crystalline material was collected by filtration
  10. washwashed with n-butyl acetate
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-ceff208f793f4ad1beba14b01695d80b
Source dataset
uspto-grants-2001_01
Patent number
US06180665B2

Reaction notes

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