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CAS No. : | 77128-73-5 | MDL No. : | MFCD00151938 |
Formula : | C25H23NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GBROUWPNYVBLFO-QHCPKHFHSA-N |
M.W : | 401.45 | Pubchem ID : | 978356 |
Synonyms : |
|
Chemical Name : | (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Fmoc-Rink-PEGA800 resin (0.8 g, L = 0.4 mmol/g, 0.32 mmol) was Fmoc deprotectedand washed with DMF (x5). Fmoc-N-Me-Phe-OH (385 mg, 0.96 mmol) was coupled viaTBTU (295 mg, 0.92 mmol) with NEM (365 pL, 1.28 mmol) in dry DMF. The resin waswashed with DMF (x5), Fmoc deprotected and washed with DMF (x5). Na-Boc-L-aminobutyric acid (195 mg, 0.96 mmol) was then similarly coupled via TBTU. Washwith DMF (x5), DCM (x2) and CH3CN (x2) followed by lyophilization. The dipeptideamide was cleaved from the resin by treatment with TFA:TIPS 95:5 for 30 min. followedby wash with TFA:TIPS 95:5 (x5). The combined fractions were concentrated in vacuoand the resulting oil was lyophilized. The amino group was re-protected with Boc byreaction with Boc2O (139 mg, 0.32 mmol) and DIPEA (53 juL, 0.38 mmol) in dry CH3CN(2 mL) at rt o.n. Purification by HPLC gave the Boc-protected dipeptide amide as awhite residue (18 mg, 15percent). The amide was dehydrated with POCI3/pyridine/imidazole(15 |iL/1.2 mL/4.7 mg) and subsequently Boc-deprotected as described in example 2.Purification by HPLC gave the title compound as a white solid. |
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