Diisopropylethylamine → N-[(2-Adamantyloxy)carbonyl]-alpha-trimethylsilylethoxymethyl-DL-tryptophan methyl ester

HRID 54861Notes

Reaction equation

HRID 54861 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[NH:5][CH2:6][O:7][CH:8]([Si:10]([CH3:13])([CH3:12])[CH3:11])[CH3:9].C(N(C(C)C)CC)(C)C.[CH:34]12[CH2:43][CH:38]3[CH2:39][CH:40]([CH2:42][CH:36]([CH2:37]3)[CH:35]1[O:44][C:45](Cl)=[O:46])[CH2:41]2>C1COCC1.O>[CH3:1][O:2][C:3](=[O:24])[CH:4]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[N:5]([CH2:6][O:7][CH:8]([Si:10]([CH3:13])([CH3:12])[CH3:11])[CH3:9])[C:45]([O:44][CH:35]1[CH:34]2[CH2:43][CH:38]3[CH2:39][CH:40]([CH2:42][CH:36]1[CH2:37]3)[CH2:41]2)=[O:46]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 108785372-adamantyl ChloroformateHCID 86747504alpha-trimethylsilylethoxymethyl-DL-tryptophan methyl ester

Product 1

HCID 86747503N-[(2-Adamantyloxy)carbonyl]-alpha-trimethylsilylethoxymethyl-DL-tryptophan methyl esterYield 67.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of α-trimethylsilylethoxymethyl-DL-tryptophan methyl ester (1.0 g, 2.8 mmol), diisopropylethylamine (0.4 g, 3 mmol) and 2-adamantylchloroformate (0.65 g, 3 mmol) in 20 mL dry THF was stirred at room temperature for 4 hours. The reaction mixture was diluted with distilled water and extracted with ethyl acetate (4×50 mL). The organic extract was washed with brine and dried over Na2SO4. Evaporation of the organic solvent gave the title compound as a colorless foam (1.0 g, 67.8%).

Workup

  1. extractionextracted with ethyl acetate (4×50 mL)
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation of the organic solvent

Sources & evidence

ORD record
ord-ae8aefd7edf6448d89ace837ceea7eed
Source dataset
uspto-grants-1997_04
Patent number
US05622983

Reaction notes

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