Chlorosuccinimide → (R)-5-[4-((R)-2,3-Dihydroxy-propoxy)-phenyl]-3-{(1S,2S)-1-[5-(2-fluoro-4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-imidazolidine-2,4-dione

HRID 561987

반응식

HRID 561987 반응식
IC1C=CC(C2NC([C@@H](N3[C:21](=[O:22])[C@@H](CCC(O)=O)NC3=O)C(C)C)=NC=2)=CC=1.ClN1C(=O)CCC1=O.C(OC(=O)N[C@H](C1NC(C2C=CC=CC=2F)=CN=1)[C@H](C1C=CC=CC=1)C)(C)(C)C.C(OC(N[C@H](C1C=CC(OCC(=O)N(C)C)=CC=1)C(O)=O)=O)(C)(C)C.[NH2:91][C@H:92]([C:118]1[CH:123]=[CH:122][C:121]([O:124][CH2:125][C@H:126]([OH:129])[CH2:127][OH:128])=[CH:120][CH:119]=1)[C:93]([NH:95][C@H:96]([C:105]1[NH:106][C:107]([C:110]2[CH:115]=[CH:114][C:113]([I:116])=[CH:112][C:111]=2[F:117])=[CH:108][N:109]=1)[C@H:97]([C:99]1[CH:104]=[CH:103][CH:102]=[CH:101][CH:100]=1)[CH3:98])=[O:94]>>[OH:129][C@H:126]([CH2:127][OH:128])[CH2:125][O:124][C:121]1[CH:122]=[CH:123][C:118]([C@H:92]2[NH:91][C:21](=[O:22])[N:95]([C@H:96]([C:105]3[NH:106][C:107]([C:110]4[CH:115]=[CH:114][C:113]([I:116])=[CH:112][C:111]=4[F:117])=[CH:108][N:109]=3)[C@H:97]([C:99]3[CH:100]=[CH:101][CH:102]=[CH:103][CH:104]=3)[CH3:98])[C:93]2=[O:94])=[CH:119][CH:120]=1

참가 물질

6

반응물 5

HCID 31398ChlorosuccinimideHCID 577719783-((R)-1-{(S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-methyl-propyl}-2,5-dioxo-imidazolidin-4-yl)-propionic acidHCID 66815126(R)-tert-butoxycarbonylamino-(4-dimethylcarbamoylmethoxy-phenyl)-acetic acidHCID 67001596(R)-2-amino-2-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-N-{(1S,2S)-1-[5-(2-fluoro-4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-acetamideHCID 67001749{(1S,2S)-1-[5-(2-fluoro-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-carbamic acid tert-butyl ester

생성물 1

HCID 57771930(R)-5-[4-((R)-2,3-Dihydroxy-propoxy)-phenyl]-3-{(1S,2S)-1-[5-(2-fluoro-4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-imidazolidine-2,4-dione

실험 절차

Prepared by the same method as described in example 1 except that (i) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step F was omitted; (ii) (R)-tert-butoxycarbonylamino-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acid (prepared as described in example 33) was used in place of (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid in step 36-G, and (iii) cyclization of (R)-2-amino-2-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-N-{(1S,2S)-1-[5-(2-fluoro-4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-acetamide in step 36-H was performed as described in example 34. HR-MS: calcd for C30H28FlN4O5 [M+H+] 671.1161. Found 671.1156.

후처리

  1. customPrepared by the same method

출처 및 근거

ORD 기록
ord-766ec25cfe3f47a3a30c9dc4900d5549
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063085B2

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