Trifluoroacetic acid → Z-Phe-Ser(OCH2C6H5)-Ala-OCH3

HRID 236468

반응식

HRID 236468 반응식
[NH:1]([C:15]([O:17]C(C)(C)C)=O)[C@H:2]([C:12]([OH:14])=O)[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:22][C@H:23]([C:25]([O:27][CH3:28])=[O:26])[CH3:24].Cl.N(C(OC(C)(C)C)=O)[C@H](C(N[C@H](C(OC)=O)C)=O)COCC1C=CC=CC=1.FC(F)(F)C(O)=O.N[C@H](C(N[C@H](C(OC)=O)C)=O)COCC1C=CC=CC=1.FC(C(O)=O)(F)F.[NH:91]([C:103]([O:105][CH2:106][C:107]1[CH:112]=[CH:111][CH:110]=[CH:109][CH:108]=1)=[O:104])[C@H:92](C(O)=O)[CH2:93][C:94]1[CH:99]=[CH:98][CH:97]=[CH:96][CH:95]=1>>[NH:91]([C:103]([O:105][CH2:106][C:107]1[CH:112]=[CH:111][CH:110]=[CH:109][CH:108]=1)=[O:104])[C@H:92]([C:15]([NH:1][C@H:2]([C:12]([NH:22][C@H:23]([C:25]([O:27][CH3:28])=[O:26])[CH3:24])=[O:14])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:17])[CH2:93][C:94]1[CH:99]=[CH:98][CH:97]=[CH:96][CH:95]=1

참가 물질

7

반응물 6

HCID 6422Trifluoroacetic acidHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 2733257Alanine methyl ester hydrochlorideHCID 54537467Boc-Ser(OCH2C6H5)-Ala-OCH3HCID 131715028H-Ser(OCH2C6H5)-Ala-OCH3 trifluoroacetate

생성물 1

HCID 131715027Z-Phe-Ser(OCH2C6H5)-Ala-OCH3수율 74%

실험 절차

First, Boc-Ser(OCH2C6H5)-OH (4.93 g, 16.7 mmol) was coupled to H-Ala-OCH3.HCl (2.80 g, 20.0 mmol) by a mixed anhydride procedure to yield an oil, 6.1 g. Boc-Ser(OCH2C6H5)-Ala-OCH3 was then deblocked with trifluoroacetic acid, and the resulting product, H-Ser(OCH2C6H5)-Ala-OCH3 trifluoroacetate (6.15 g, 15.6 mmol), was coupled to Z-Phe-OH (3.89 g, 13.0 mmol) using a mixed anhydride procedure. This product was crystallized from ethyl acetate to yield 5.4 g of Z-Phe-Ser(OCH2C6H5)-Ala-OCH3 (m.p. 158°-159°).

후처리

  1. customto yield an oil, 6.1 g
  2. customThis product was crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-855efd086c324e4189391e3f005dbaac
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04644055

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