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With 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride; In dichloromethane; at 0 - 20℃; for 61h;
Examples 2-10. Preparation of 4-fluoropyrrolidine-2-carbonyl fluoride compounds (Ia), (Ib), (Ic), (Id), and (If).[0086] 4-Fluoropyrrolidine-2-carbonyl fluoride compounds (Ia), (Ib), (Ic), (Id), and(If) were prepared by reaction of the corresponding 4-hydroxypyrrolidine-2-carboxylic acid compound with a fluorinating agent in the same manner as described in Example 1. The results and reaction conditions are shown in Table 3 together with those of Example 1.
2-chlorotrityl chloride polystyrene resin[ No CAS ]
[ 850863-89-7 ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-31-6 ]
[ 71989-33-8 ]
[ 71989-18-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 143824-78-6 ]
[ 189249-10-3 ]
H-Gly-Thr(OtBu)-Cys(Trt)-Asn(Trt)-Thr(OtBu)-Pro-Gly-Cys(Trt)-Thr(OtBu)-Cys(Trt)-Ser(OtBu)-Trp(Boc)-[(4S)-4-hydroxy-L-proline]-Val-Cys(Trt)-Thr(OtBu)-Arg(Pbf)-Asn(Trt)-Gly-Leu-Pro-Val-Cys(Trt)-Gly-Glu(OtBu)-Thr(OtBu)-Cys(Trt)-Val-Gly-OH[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
General procedure: Solid phase peptide synthesis Linear peptides were synthesized on 2-chlorotrityl chloride (2CTC) resin. Couplings were performed using 4 equiv of Fmoc-protected amino acid, 3 equiv of O-(1H-6-chlorobenzotriazol-1-y1)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HCTU), and 6 equiv of N,N-diisopropylethylamine (DIPEA) in dimethylformamide (DMF) for 2*10 min. Fmoc deprotection was carried out with 30% (v/v) piperidine in DMF. After each coupling and deprotection step, the peptide-resin was washed with DMF (3*), dichloromethane (DCM) (3*), and DMF (3*). The peptide-resin was treated with 1% (v/v) TFA (trifluoroacetic acid) in DCM (5 mL for 5 min, 10 times), draining the vessel after each cycle into a 1:1 mixture of MeCN/H2O (100 mL). DCM was removed in vacuo and the solutions lyophilized to afford the crude linear peptide.
H-DPro-(4S)Hyp-Glu-NH2 *TFA; Hyp=hydroxyproline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
General procedure: i-Pr2NEt (6 equiv) was added to a solution of Fmoc-Xaa-OH (3 equiv)and HATU (3 equiv) in a minimal amount of DMF necessary to obtaina solution. The solution of the activated amino acid (?100 mM) was the mixture was agitated for 1 h before washing with DMF (3 ×) andCH2Cl2 (3 ×).Fmoc-Deprotection; General ProcedureA solution of 20% piperidine in DMF was added to the resin pre-swollenin CH2Cl2, the reaction mixture was agitated for 10 min, drained,and the piperidine treatment was repeated for 10 min. Finally, the resin was washed with DMF (3 ×) and CH2Cl2 (3 ×).The amino acid coupling steps and the Fmoc-deprotections were monitored by qualitative Kaiser (primary amines) and chloranil tests(secondary amines). Deprotection of Side Chain Functional Groups and Cleavage of the Peptide from the Solid Support; General ProcedureA mixture of TFA/TIS/H2O (95:2.5:2.5) was added to the immobilized peptide and the suspension was agitated for 1 h and a second time for30 min. Pooling of the filtrates and removal of all volatiles under reduced pressure followed by precipitation and thorough washing with Et2O afforded the peptide as a TFA salt. The peptide was redissolved inMeCN/H2O (1:1), dried by lyophilization, and used without further purification.
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