Tryptophan, N-benzoyl-, methyl ester (7CI) synthesis

6synthesis methods

Product Name:Tryptophan, N-benzoyl-, methyl ester (7CI)
CAS Number:2717-75-1
Molecular formula:C19H18N2O3
Molecular Weight:322.36

65-85-0 Synthesis

65-85-0
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4299-70-1 Synthesis

4299-70-1
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$337.00/250mg

Tryptophan, N-benzoyl-, methyl ester (7CI)

2717-75-1
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91827-25-7
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Yield:82 % ee

Reaction Conditions:

with tris(1,2-dioxyphenyl)cyclotriphosphazene in toluene at 128; under 760.051 Torr; for 16 h;Inert atmosphere;Dean-Stark;Overall yield = 32 percent; Overall yield = 57.77 mg;

Steps:

Amides; General Procedure

General procedure: An oven-dried 50 mL two-necked round-bottom flask was equippedwith a Teflon coated magnetic stirrer bar and connected to an azeotropiccondenser. To seal the apparatus, a balloon was connected tothe azeotropic condenser by a three-way stopcock; then, the atmospherewas replaced by N2 gas. Under a flow of N2, the flask wascharged with the CA (0.5 mmol, 1 equiv) and TAP-1 (11.48 mg, 5mol%). Then, the amine (0.5 mmol, 1 equiv) was added under N2 flow,followed by the solvent (dehydrated toluene or chlorobenzene; 7 mL).The reaction mixture was stirred under azeotropic reflux at 128 °C(133 °C in the case of chlorobenzene) for 16 h. Thereafter, the reaction flask was cooled to r.t., and the solvent was evaporated under reducedpressure using a rotary evaporator. The purification was performedby a three-step acid/base extraction. To this end, a separatory funnelwas charged with H2O and a DCM solution of the crude product mixture;after extraction, the organic layers (3 × 25 mL of DCM) were collectedand washed with sat. aq Na2CO3 (25 mL). The aqueous layerwas subsequently extracted with DCM (3 × 25 mL), and the organicphases were combined. The combined organic phases were washedwith aq HCl (1 M, 25 mL). The aqueous phase was extracted withDCM (3 × 25 mL). The combined organic layers were washed withbrine solution, dried over Na2SO4, and filtered. Finally the solvent ofthe filtrate was removed under reduced pressure.

References:

Movahed, Farzaneh Soleymani;Sawant, Dinesh N.;Bagal, Dattatraya B.;Saito, Susumu [Synthesis,2020,vol. 52,# 21,p. 3253 - 3262]

613-94-5 Synthesis