تفاعل #994632

ord-41872591e3c84e609f9e4f162c97ea1c

معادلة التفاعل

C=CCOC(=O)[C@@H](N)Cc1ccc(OC(C)(C)C)cc1
H-Tyr(tBu)-OAllyl
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HBTU
CC(C)(C)OC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
Fmoc-Ser(tBu)
CCN(C(C)C)C(C)C
DIPEA
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HBTU
→
C=CCOC(=O)[C@H](Cc1ccc(OC(C)(C)C)cc1)NC(=O)[C@H](COC(C)(C)C)NC(=O)OCC1c2ccccc2-c2ccccc21
crude material
المردود 96.0%
C=CCOC(=O)[C@H](Cc1ccc(OC(C)(C)C)cc1)NC(=O)[C@H](COC(C)(C)C)NC(=O)OCC1c2ccccc2-c2ccccc21
Fmoc-Ser(tBu)-Tyr(tBu)-OAllyl
المردود 96.0%

المتفاعلات

C=CCOC(=O)[C@@H](N)Cc1ccc(OC(C)(C)C)cc1
H-Tyr(tBu)-OAllyl
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HBTU
CC(C)(C)OC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
Fmoc-Ser(tBu)
CCN(C(C)C)C(C)C
DIPEA
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HBTU

الكواشف

لا شيء

المذيبات

CN(C)C=O
DMF

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

الإجراء التجريبي

According to the general procedure for HBTU promoted coupling, 18.26 g Fmoc-Ser(tBu), 16.95 g HBTU, 11.95 g H-Tyr(tBu)-OAllyl and 26.10 ml DIPEA were reacted in a CYTOS® Lab System in anhydrous DMF at 45° C. and at a total flow rate of 32 ml/min at residence time of 1 min to yield 26.09 g crude material (yield based on HPLC: 96%) which was used in the next step without purification.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08013117B2uspto-grants-2011_09