1,2-Dichloroethane → Benzyl(2-{[(3S)-3-{[(benzyloxy)carbonyl]amino}-6-({[(8S,11S,14S)-14-[(tert-butoxycarbonyl)amino]-11-{3-[(tert-butoxycarbonyl)amino]propyl}-9-ethyl-5,17-dihydroxy-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]henicosa-1(20),2(21),3,5,16,18-hexaen-8-yl]carbonyl}amino)hexanoyl]-amino}ethyl)carbamate

HRID 269659ノート

反応式

HRID 269659 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:27][C:26]2[CH:28]=[C:22]([CH:23]=[CH:24][C:25]=2[OH:29])[C:21]2=[CH:30][C:17](=[C:18]([OH:31])[CH:19]=[CH:20]2)[CH2:16][C@@H:15]([C:32](O)=[O:33])[N:14]([CH2:35][CH3:36])[C:13](=[O:37])[C@H:12]([CH2:38][CH2:39][CH2:40][NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[NH:11][C:10]1=[O:49])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C([N:58]([C@H:62]([CH2:67][C:68]([NH:70][CH2:71][CH2:72][NH:73][C:74]([O:76][CH2:77][C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1)=[O:75])=[O:69])[CH2:63][CH2:64][CH2:65][NH2:66])[C:59](=[O:61])[OH:60])C1C=CC=CC=1.[CH2:84](Cl)CCl.[CH:88]1[CH:89]=[CH:90][C:91]2N(O)N=N[C:92]=2[CH:93]=1>CN(C)C=O>[CH2:77]([O:76][C:74](=[O:75])[NH:73][CH2:72][CH2:71][NH:70][C:68](=[O:69])[CH2:67][C@@H:62]([NH:58][C:59]([O:60][CH2:84][C:92]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:93]=1)=[O:61])[CH2:63][CH2:64][CH2:65][NH:66][C:32]([C@H:15]1[N:14]([CH2:35][CH3:36])[C:13](=[O:37])[C@H:12]([CH2:38][CH2:39][CH2:40][NH:41][C:42]([O:44][C:45]([CH3:46])([CH3:48])[CH3:47])=[O:43])[NH:11][C:10](=[O:49])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:27][C:26]2[CH:28]=[C:22]([CH:23]=[CH:24][C:25]=2[OH:29])[C:21]2=[CH:30][C:17](=[C:18]([OH:31])[CH:19]=[CH:20]2)[CH2:16]1)=[O:33])[C:78]1[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=1

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 66879719(8S,11S,14S)-14-[(tert-Butoxycarbonyl)amino]-11-{3-[(tert-butoxycarbonyl)amino]propyl}-9-ethyl-5,17-dihydroxy-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]henicosa-1(20),2(21),3,5,16,18-hexaene-8-carboxylic acidHCID 69216382benzyl((1S)-4-amino-1-{2-[(2-{[(benzyloxy)carbonyl]amino}ethyl)amino]-2-oxoethyl}butyl)carbamate hydrochloride

生成物 1

HCID 131727163Benzyl(2-{[(3S)-3-{[(benzyloxy)carbonyl]amino}-6-({[(8S,11S,14S)-14-[(tert-butoxycarbonyl)amino]-11-{3-[(tert-butoxycarbonyl)amino]propyl}-9-ethyl-5,17-dihydroxy-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]henicosa-1(20),2(21),3,5,16,18-hexaen-8-yl]carbonyl}amino)hexanoyl]-amino}ethyl)carbamate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Under argon, 30 mg (0.044 mmol) of (8S,11S,14S)-14-[(tert-butoxycarbonyl)amino]-11-{3-[(tert-butoxycarbonyl)amino]propyl}-9-ethyl-5,17-dihydroxy-10,13-dioxo-9,12-diazatricyclo-[14.3.1.12,6]henicosa-1(20),2(21),3,5,16,18-hexaene-8-carboxylic acid (Example 170A) and 80 mg (0.162 mmol) of benzyl-((1S)-4-amino-1-{2-[(2-{[(benzyloxy)carbonyl]amino}ethyl)amino]-2-oxoethyl}butyl)carbamate hydrochloride (Example 105A) are dissolved in 2 ml of dimethylformamide. Then, at 0° C. (ice bath), 31.16 mg (0.162 mmol) of EDC and 1.95 mg (0.014 mmol) of HOBt are added. The mixture is slowly warmed to RT and stirred at 50° C. for 3 days. The solution is concentrated in vacuo and the residue is purified by preparative HPLC.

後処理

  1. concentrationThe solution is concentrated in vacuo
  2. customthe residue is purified by preparative HPLC

出典と根拠

ORDレコード
ord-77ae29f870f642e184f8a0aedda7f971
出典データセット
uspto-grants-2008_11
特許番号
US07446102B2

反応ノート

読み込み中…