* 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.
With potassium carbonate In acetonitrile at 20℃; for 2 h;
General procedure: To a solution of H-Phe-OH (100 mg, 60.5 mmol) in 50 percent MeCN (6.1 mL)were added Fmoc-OPhth (233 mg, 60.5 mmol) and K2CO3 (167 mg, 121 mmol) and stirred at room temperature. After 2 h of stirring saturated sodium bicarbonate solution and H2O were added and the resulting solution was washed with diethyl ether. The aqueous phase is acidified to pH 1 with 1M HCl and extracted with diethyl ether. The organic phase was washed with 1 M HCl, H2O, brine, dried over MgSO4. The filtrate was evaporatedevaporated under reduced pressure to give yellow solid as crude product.
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1995, # 4, p. 723 - 730
[2] Synthetic Communications, 2009, vol. 39, # 11, p. 2022 - 2031
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 2980 - 2983
[4] Tetrahedron Letters, 2017, vol. 58, # 16, p. 1600 - 1603
5
[ 61-90-5 ]
[ 28920-43-6 ]
[ 35661-60-0 ]
Reference：
[1] Journal of Organic Chemistry, 1972, vol. 37, # 22, p. 3404 - 3409
[2] Journal of the Chinese Chemical Society, 2011, vol. 58, # 4, p. 509 - 515
[3] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 592 - 609
6
[ 28920-43-6 ]
[ 35661-60-0 ]
Reference：
[1] Helvetica Chimica Acta, 1992, vol. 75, # 8, p. 2572 - 2582
[2] Patent: US4128540, 1978, A,
[3] Synlett, 2011, # 14, p. 2013 - 2016
EXAMPLE 22 N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-leucine Amide (NPC 15528) A solution of N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine, acid chloride (3.5 g, 10 mmol) in 10 mL of THF was charged with NH3 (29.6percent water solution, 1.26 mL, 20 mmol) at room temperature. The reaction mixture was stirred for 30 min., then diluted with 100 mL of water and extracted with ethyl acetate (5*20 mL). The organic layers were combined, extracted with 10percent potassium carbonate solution, washed with water, brine, dried and evaporated. Recrystallization of the product from ethanol afforded 1.26 g (36percent) of N-(9-fluorenylmethoxycarbonyl)-L-leucine, amide as colorless solid, mp 79°-80° C.
Reference：
[1] Patent: US5079260, 1992, A,
10
[ 61-90-5 ]
[ 1131148-55-4 ]
[ 35661-60-0 ]
Reference：
[1] Synlett, 2011, # 14, p. 2013 - 2016
11
[ 61-90-5 ]
[ 35661-60-0 ]
Reference：
[1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 10, p. 3103 - 3108
12
[ 61-90-5 ]
[ 88744-04-1 ]
[ 35661-60-0 ]
Reference：
[1] Synthesis, 1986, # 4, p. 303 - 305
13
[ 61-90-5 ]
[ 102774-86-7 ]
[ 35661-60-0 ]
Reference：
[1] Liebigs Annalen der Chemie, 1988, p. 1095 - 1098
Stage #1: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 0℃; for 0.166667 h; Stage #2: With sodium tetrahydroborate In water; ethyl acetate at 0℃; for 0.4 h;
General procedure: To a solution of carboxylic acid (10 mmol) in THF (10 mL), DIPEA (11 mmol, 1.42 mL) and 50percent T3P in EtOAc (20 mmol, 6.36 mL) were added at 0 °C and the solution was stirred for about 10 min. Then aqueous solution of NaBH4 (10 mmol, 388 mg in 0.3 mL of H2O) was added to the reaction mixture at the same temperature and the reaction was allowed to stir till the completion of the reaction as indicated by TLC. After the completion of the reaction, the solvent was evaporated and the crude alcohol was extracted into EtOAc and the organic phase was washed with 5percent citric acid (10 mL .x. 2), 5percent Na2CO3 (10 mL .x. 2), water, and brine solution. The product was isolated after the evaporation of solvent under reduced pressure and dried over anhydrous Na2SO4.
Reference：
[1] Journal of Organic Chemistry, 2001, vol. 66, # 25, p. 8454 - 8462
[2] Angewandte Chemie - International Edition, 2010, vol. 49, # 1, p. 117 - 120
[3] Organic and Biomolecular Chemistry, 2010, vol. 8, # 21, p. 4855 - 4860
[4] Tetrahedron Letters, 2012, vol. 53, # 38, p. 5059 - 5063
[5] Organic Letters, 2008, vol. 10, # 10, p. 1881 - 1884
[6] Organic and Biomolecular Chemistry, 2011, vol. 9, # 11, p. 4182 - 4187
[7] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 6994 - 6996
[8] Tetrahedron Asymmetry, 1998, vol. 9, # 11, p. 1855 - 1858
[9] Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5260 - 5266
[10] Synthetic Communications, 2009, vol. 39, # 19, p. 3555 - 3566
[11] Synlett, 2010, # 5, p. 715 - 720
[12] Organic and Biomolecular Chemistry, 2011, vol. 9, # 11, p. 4182 - 4187
[13] ChemMedChem, 2013, vol. 8, # 7, p. 1041 - 1056
[14] ACS Combinatorial Science, 2017, vol. 19, # 3, p. 131 - 136
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[ 35661-60-0 ]
[ 139551-83-0 ]
Reference：
[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4581 - 4589
28
[ 186581-53-3 ]
[ 35661-60-0 ]
[ 193887-44-4 ]
Reference：
[1] Chemical communications (Cambridge, England), 2001, # 22, p. 2330 - 2331
(2S,3R)-3-tert-Butoxy-2-[(S)-3-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-butyric acid 2-trimethylsilanyl-ethyl ester[ No CAS ]
(S)-N-{(1S,2R)-2-Hydroxy-1-[2-(4-methoxy-phenyl)-ethylcarbamoyl]-propyl}-3-{(S)-2-[(isoquinoline-3-carbonyl)-amino]-4-methyl-pentanoylamino}-succinamic acid[ No CAS ]
Fmoc-L-α,γ-diaminobutyryl(2-ClZ)-Thr(Bzl)-L-α,γ-diaminobutyryl(2-ClZ)-L-α,γ-diaminobutyryl-L-α,γ-diaminobutyryl(2-ClZ)-d-Phe-Leu-L-α,γ-diaminobutyryl(2-ClZ)-L-α,γ-diaminobutyryl(2-ClZ)-Thr(Bzl)-OH[ No CAS ]
Chelmical synthesis: Peptides were synthesized on a Rink amide resin, 0.45 mmol/g [Fmoc-Cys(Trityl)-Wang; Novabiochem, San Diego, Calif.] usinig N-(9-fluorenyl)methoxycarboxyl chemistry and standard side chain protection except on cysteine residues. Cysteine residues were protected in pairs with either S-trityl on the first and third cysteines or S-acetamidomethyl on the second and fourth cysteines. Amino acid derivatives were from Advanced Chemtech (Louisville, Ky.). The peptides were removed from the resin and precipitated, and a two-step oxidation protocol was used to selectively fold the peptides as described previously (Luo et al., 1999). Briefly, the first disulfide bridge was closed by dripping the peptide into an equal volume of 20 mM potassium feliicyanide and 0.1 M Tris, pH 7.5. The solution was allowed to react for 30 min, and the monocyclic peptide was purified by reverse-phase HPLC. Simultaneous removal of the S-acetamidomethyl groups and closure of the second disulfide bridge was carried out by iodine oxidation. The monocyclic peptide and HPLC eluent was dripped into an equal volume of iodine (10 mM) in H20/trifluoroacetic acid/acetonitrile (78:2:20 by volume) and allowed to react for 10 min. The reaction was terminated by the addition of ascorbic acid diluted 20-fold with 0.1percent trifluoroacetic acid and the bicyclic product purified by HPLC. Mass Spectrometry: Measurements were performed at the Salk Institute for Biological Studies (San Diego, Calif.) under the direction of Jean Rivier. Matrix-assisted laser desorption ionization time-of-flight mass spectrometry and liquid secondary ionization mass spectrometry were used.
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