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 269659노트

반응식

HRID 269659 반응식
[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

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-77ae29f870f642e184f8a0aedda7f971
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446102B2

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