(R)-4-Benzyl-2-oxazolidinone → 3-(2-(R)-cyclopropylmethyl-5-(3,5-difluorophenyl)-3 (S)-hydroxyl-1-oxopentyl)amino-1-methyl-5-(pyridin-2-yl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

HRID 30305

反応式

HRID 30305 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH:11]=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1.FC1C=C(C=C(F)C=1)/C=C/C(O)=O.C1(C[C@@H]2COC(=O)[NH:34]2)C=CC=CC=1.FC1C=C(CCC(O)=O)C=C(F)C=1.[O:52]=[C:53]1[C@@H:59]([NH:60][C:61](=[O:79])[C@H:62]([CH2:75][CH:76]2[CH2:78][CH2:77]2)[C@@H](O)CCC2C=C(F)C=C(F)C=2)CCC[CH2:55][N:54]1CC1C=CC=C(OC2C=CC=CC=2)C=1.C1(C[C@H:100]([C@@H:116](O)[CH2:117]CC2C=CC=CC=2)[C:101]([N:103]2[C@H:107]([CH2:108][C:109]3[CH:114]=[CH:113][CH:112]=[CH:111][CH:110]=3)COC2=O)=O)CCCC1>>[CH:76]1([CH2:75][C@H:62]([C@@H:11]([OH:12])[CH2:10][CH2:9][C:4]2[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=2)[C:61]([NH:60][CH:59]2[N:34]=[C:108]([C:107]3[CH:117]=[CH:116][CH:100]=[CH:101][N:103]=3)[C:109]3[CH:110]=[CH:111][CH:112]=[CH:113][C:114]=3[N:54]([CH3:55])[C:53]2=[O:52])=[O:79])[CH2:78][CH2:77]1

参加物

7

反応物 6

HCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 36694983-(3,5-Difluorophenyl)propionic acidHCID 5374941trans-3,5-Difluorocinnamic acidHCID 160925303-(3,5-Difluorophenyl)propanalHCID 183467703-(2 (R)-cyclopentylmethyl-3(S)-hydroxyl-5-phenyl-1-oxopentyl)-4(R)-(phenylmethyl)-2-oxazolidinoneHCID 675500392(R)-cyclopropylmethyl-5-(3,5-difluorophenyl)-3-(S)-hydroxypentanoic acid (2-oxo-1-(3-phenoxybenzyl)azapan-3-(S)-yl)amide

生成物 1

HCID 98070773-(2-(R)-cyclopropylmethyl-5-(3,5-difluorophenyl)-3 (S)-hydroxyl-1-oxopentyl)amino-1-methyl-5-(pyridin-2-yl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

実験手順

The 3-(3,5-difluorophenyl)propanal used in the aldol reaction was prepared from trans-3,5-difluorocinnamic acid by: (1) hydrogenation to 3-(3,5-difluorophenyl)propionic acid (L. Kruse et al J. Med. Chem. 1987, 30, 486-494); (2) formation of Weinreb amide (M. Braun Synthesis 1989, 856); and (3) reduction to aldehyde (D. A. Evans J. Org. Chem. 1993, 58, 2446-2453).

出典と根拠

ORDレコード
ord-767ee72b508949e0b1fe683c50924b03
出典データセット
uspto-grants-2008_09
特許番号
US07423033B2

関連ノート

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