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 269659Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269659
[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

Komponenten

6

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-77ae29f870f642e184f8a0aedda7f971
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446102B2

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