Chlorotrimethylsilane → (R)-3-{(S)-1-[5-(4-Iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-ethyl}-5-prop-2-ynyl-imidazolidine-2,4-dione

HRID 561980

반응식

HRID 561980 반응식
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]([N:17]3[C:21](=[O:22])[C@@H:20]([CH2:23][CH2:24][C:25](O)=O)[NH:19][C:18]3=[O:28])[CH:14]([CH3:16])C)=[N:10][CH:9]=2)=[CH:4][CH:3]=1.C(OC(=O)N[C@H:36]([C:45]1NC(C2C=CC=CC=2F)=CN=1)[C@H:37]([C:39]1C=CC=C[CH:40]=1)C)(C)(C)C.IC1C=CC(C(=O)C)=CC=1.C(OC(N[C@H](C1C=CC(OCC(=O)N(C)C)=CC=1)C(O)=O)=O)(C)(C)C.ClN1C(=O)CCC1=O.C(OC(N[C@H](CC#C)C(O)=O)=O)(C)(C)C.FC(F)(F)C(O)=O.Cl[Si](C)(C)C>C(N(CC)CC)C.C(O)=O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][C:11]([C@@H:13]([N:17]3[C:21](=[O:22])[C@@H:20]([CH2:23][C:24]#[CH:25])[NH:19][C:18]3=[O:28])[CH2:14][C:16]3[CH:40]=[CH:39][CH:37]=[CH:36][CH:45]=3)=[N:10][CH:9]=2)=[CH:6][CH:7]=1

참가 물질

11

반응물 8

HCID 6397ChlorotrimethylsilaneHCID 6422Trifluoroacetic acidHCID 31398ChlorosuccinimideHCID 728691-(4-Iodophenyl)ethan-1-oneHCID 7009126(2R)-2-(((tert-butoxy)carbonyl)amino)pent-4-ynoic acidHCID 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 acid2회HCID 67001749{(1S,2S)-1-[5-(2-fluoro-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-carbamic acid tert-butyl ester

생성물 1

HCID 57771957(R)-3-{(S)-1-[5-(4-Iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-ethyl}-5-prop-2-ynyl-imidazolidine-2,4-dione

시약·촉매·용매 2

HCID 284Formic Acid용매HCID 8471Triethylamine용매

실험 절차

Prepared by the same method as described in example 1 except that (i) steps A, B, and C were omitted; (ii) commercially available 1-(4-iodo-phenyl)-ethanone was used in place of 1-(2-fluoro-4-iodo-phenyl)-ethanone in step 18-D; (iii) (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid was used in place of (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid in step 18-E; (iv) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 18-F was omitted; (v) (R)-2-tert-butoxycarbonylamino-pent-4-ynoic acid was used in place of (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid in step 18-G; and (vi) in step 18-H, formic acid (neat) heated to 30° C. was used in place of trifluoroacetic acid and silylation with chlorotrimethylsilane and triethylamine was omitted. HR-MS: calcd for C23H19IN4O2 [M+H+] 511.0626. Found 511.0623.

후처리

  1. customPrepared by the same method

출처 및 근거

ORD 기록
ord-2b33d7d6a5364198ae27a67094cfe5af
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063085B2

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