HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1634916Generated: October 25, 2026
L-Tryptophan → N-[(phenylmethoxy)carbonyl]-L-tryptophan 1,1-dimethylethyl ester
https://huagongshe.com/reaction/1634916
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | L-Tryptophan | HCID 6305 | — |
| Reactant | Benzyl chloroformate | HCID 10387 | — |
| Reactant | t-Butyl bromide | HCID 10485 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | benzyloxycarbonyl-L-tryptophan | HCID 101176 | — |
| Catalyst | Benzyl triethylammonium chloride | HCID 66133 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | N-[(phenylmethoxy)carbonyl]-L-tryptophan 1,1-dimethylethyl ester | HCID 15600488 | 99% |
Reaction Steps
To a suspension of N-[(phenylmethoxy)carbonyl]-L-tryptophan (33.27 g; 98.32 mol) (previously prepared by reacting L-tryptophan with CBZCl, in H2O and 1N NaOH), benzyltriethylammonium chloride (BTEAC) (22.4 g; 98.32 mol) and K2CO3 (176.91 g; 1.28 mol) in dimethylacetamide (750 mL) is added tert-butyl bromide (265 mL; 2.36 mol). The solution is heated to 55° C. and vigorously stirred for 19 hours. The mixture is then cooled to room temperature, diluted with H2O (3L) and then extracted with EtOAc (2×1L). The organic phases are evaporated to dryness to obtain the title product as a pale yellow oil (36 g; 98 mol)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06509324B1 |
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| Source dataset | uspto-grants-2003_01 |
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| ORD ID | ord-7abfc88921c243fe8a28fbfcf4ce1e90 |
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| Source note | uspto-grants-2003_01 |
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