반응식
C([O:8][C:9](=[O:20])[C@H:10]([CH2:12][C:13]1[CH:18]=[CH:17][C:16](O)=[CH:15][CH:14]=1)[NH2:11])C1C=CC=CC=1.N[C@H:22](C(C(CN1C2C=CC=CC=2C(C2C=CC=CC=2)=NC(NC(=O)[C@H](CC2C=CC(OP(O)(O)=O)=CC=2)NC(=O)C)C1=O)=O)=O)[CH2:23]CSC.C(OC(=O)C)(=O)C.N[C@H](C(O)=O)CC1C=CC(O)=CC=1.C1(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)C=CC=CC=1.C([Sn](CCCC)(CCCC)CCCC)=C.[Cl-].[Li+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:22]([C:16]1[CH:15]=[CH:14][C:13]([CH2:12][C@@H:10]([C:9]([OH:8])=[O:20])[NH2:11])=[CH:18][CH:17]=1)=[CH2:23]참가 물질
9
반응물 7
HCID 6057L-Tyrosine
HCID 7918Acetic Anhydride
HCID 81998Tributylvinyltin
HCID 104541(S)-Benzyl 2-amino-3-(4-hydroxyphenyl)propanoate
HCID 142176Phenyl triflimide
HCID 433294Lithium Chloride
HCID 1317207511,3-Dihydro-1-[(L-methionyl)-carbonylmethyl)-5-phenyl-3(R,S)-{[(N-acetyl)-phosphono-L-tyrosyl]amino}-2H-1,4-benzodiazepin-2-one생성물 1
시약·촉매·용매 1
실험 절차
As illustrated by FIG. 5H, tyrosine benzyl ester 111 can be converted to N-acetyltyrosine benzyl ester (2) using acetic anhydride, with the hydroxy group of the tyrosine being transformed into the trifluoromethyl sufonyl derivative 113 by using phenyl bis[(trifluoromethyl)sulfonyl]amine. Compound 113 this can be coupled to vinyltributyltin in the presence of bis(triphenylphosphine)palladium dichloride and lithium chloride to give the 4-ethenylphenylalanine derivative 114. This product, on refluxing with catechol borane and further transesterification with pinanediol, gives p-boronoethyl-2-phenylalanine derivative 116. Catalytic hydrogenation affords 117, which can be further coupled to yield the desired peptide or peptidomimetic.
출처 및 근거
- ORD 기록
- ord-b31fff8e460e4b159eb82be68f0cac62
- 출처 데이터셋
- uspto-grants-1998_07
- 특허 번호
- US05776902
연결된 노트
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