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 → tert-Butyl{3-[(8S,11S,14S)-8-[({(4S)-4-amino-6-[(2-aminoethyl)amino]-6-oxohexyl}amino)carbonyl]-14-[(tert-butoxycarbonyl)amino]-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-11-yl]propyl}carbamate

HRID 269660Notes

Reaction equation

HRID 269660 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][NH:13][C:14](=[O:80])[CH2:15][C@@H:16]([NH:69]C(OCC1C=CC=CC=1)=O)[CH2:17][CH2:18][CH2:19][NH:20][C:21]([C@H:23]1[N:41]([CH2:42][CH3:43])[C:40](=[O:44])[C@H:39]([CH2:45][CH2:46][CH2:47][NH:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[NH:38][C:37](=[O:56])[C@@H:36]([NH:57][C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH2:35][C:34]2[CH:65]=[C:30]([CH:31]=[CH:32][C:33]=2[OH:66])[C:29]2=[CH:67][C:25](=[C:26]([OH:68])[CH:27]=[CH:28]2)[CH2:24]1)=[O:22])C1C=CC=CC=1>C(O)C.[Pd]>[C:52]([O:51][C:49](=[O:50])[NH:48][CH2:47][CH2:46][CH2:45][C@@H:39]1[NH:38][C:37](=[O:56])[C@@H:36]([NH:57][C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH2:35][C:34]2[CH:65]=[C:30]([CH:31]=[CH:32][C:33]=2[OH:66])[C:29]2=[CH:67][C:25](=[C:26]([OH:68])[CH:27]=[CH:28]2)[CH2:24][C@@H:23]([C:21]([NH:20][CH2:19][CH2:18][CH2:17][C@H:16]([NH2:69])[CH2:15][C:14]([NH:13][CH2:12][CH2:11][NH2:10])=[O:80])=[O:22])[N:41]([CH2:42][CH3:43])[C:40]1=[O:44])([CH3:53])([CH3:54])[CH3:55]

Participants

4

Reactant 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

Product 1

HCID 131727164tert-Butyl{3-[(8S,11S,14S)-8-[({(4S)-4-amino-6-[(2-aminoethyl)amino]-6-oxohexyl}amino)carbonyl]-14-[(tert-butoxycarbonyl)amino]-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-11-yl]propyl}carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

14.5 mg (0.013 mmol) of 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 (Example 176A) are dissolved in 3 ml of ethanol. 15 mg of palladium on activated carbon (10%) are added thereto, and the mixture is then hydrogenated under atmospheric pressure for 15 h. The reaction mixture is filtered through prewashed kieselguhr, and the filtrate is concentrated on a rotary evaporator in vacuo. The crude product is reacted without further purification.

Workup

  1. filtrationThe reaction mixture is filtered through prewashed kieselguhr
  2. concentrationthe filtrate is concentrated on a rotary evaporator in vacuo
  3. customThe crude product is reacted without further purification

Sources & evidence

ORD record
ord-7d7d11cae46f4349a49e86addbede5c3
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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