Hydrochloric Acid → N-[(1,1-Dimethylethoxy)carbonyl]-D-tryptophan methyl ester

HRID 429730Notes

Reaction equation

HRID 429730 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl.[CH3:16][O:17][C:18](=[O:31])[C@@H:19]([CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)[NH2:20].Cl.[O:33]1CCC[CH2:34]1>>[CH3:16][O:17][C:18](=[O:31])[C@@H:19]([CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)[NH:20][C:34]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:33]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 8028Tetrahydrofuran2×HCID 81531DiisopropylethylamineHCID 11448200methyl (2R)-2-amino-3-(1H-indol-3-yl)propanoate hydrochloride

Product 1

HCID 7188267N-[(1,1-Dimethylethoxy)carbonyl]-D-tryptophan methyl ester

Procedure

10 g of tert-butanol, 10.1 g of BOC-anhydride and 12.27 g of diisopropylethylamine dissolved in 30 ml of tetrahydrofuran are added at 0° to a suspension of 12.12 g of D-tryptophan methyl ester hydrochloride in 80 ml of abs. tetrahydrofuran. After being stirred for two hours at room temperature, the reaction mixture is poured into ice/470 ml of 0.3N HCl and extracted three times with ethyl acetate. The combined organic phases are washed once with water and twice with sat. NaCl solution, dried (MgSO4) and concentrated by evaporation. The residue is made into a slurry in diethyl ether/petroleum ether and filtered with suction. The title compound is thus obtained in the form of colourless crystals having a melting point of 148-1490. Rf (methylene chloride)=0.24.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic phases are washed once with water and twice with sat. NaCl solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated by evaporation
  5. filtrationfiltered with suction

Sources & evidence

ORD record
ord-390609a249c742b896e014337d30a9c9
Source dataset
uspto-grants-2001_11
Patent number
US06319917B1

Reaction notes

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