Ethyl Acetate → HCID 117735771, compound

HRID 1482260Notes

Reaction equation

HRID 1482260 reaction equation
[NH2:1][C:2](=[O:106])[CH2:3][NH:4][C:5](=[O:105])[C@@H:6]([NH:13][C:14](=[O:104])[C@@H:15]([N:17]([CH3:103])[C:18]([C@H:20]([CH2:92][C:93]([O:95]CC1C=CC=CC=1)=[O:94])[NH:21][C:22](=[O:91])[C@H:23]([CH2:84][C:85]1[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=1)[NH:24][C:25](=[O:83])[C@H:26]([CH:80]([CH3:82])[CH3:81])[NH:27][C:28](=[O:79])[C@H:29]([CH3:78])[NH:30][C:31](=[O:77])[C@H:32]([CH2:73][CH:74]([CH3:76])[CH3:75])[NH:33][C:34](=[O:72])[CH2:35][NH:36][C:37](=[O:71])[C@H:38]([CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[N:39]([CH3:63])[C:40](=[O:62])[C@H:41]([CH3:61])[NH:42][C:43](=[O:60])[C@H:44]([CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:19])[CH3:16])[CH2:7][O:8][C:9]([CH3:12])([CH3:11])[CH3:10].C(OCC)(=O)C.[H][H]>CO.O[Pd].[C]>[NH2:1][C:2](=[O:106])[CH2:3][NH:4][C:5](=[O:105])[C@@H:6]([NH:13][C:14](=[O:104])[C@@H:15]([N:17]([CH3:103])[C:18]([C@H:20]([CH2:92][C:93]([OH:95])=[O:94])[NH:21][C:22](=[O:91])[C@H:23]([CH2:84][C:85]1[CH:86]=[CH:87][CH:88]=[CH:89][CH:90]=1)[NH:24][C:25](=[O:83])[C@H:26]([CH:80]([CH3:82])[CH3:81])[NH:27][C:28](=[O:79])[C@H:29]([CH3:78])[NH:30][C:31](=[O:77])[C@H:32]([CH2:73][CH:74]([CH3:75])[CH3:76])[NH:33][C:34](=[O:72])[CH2:35][NH:36][C:37](=[O:71])[C@H:38]([CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[N:39]([CH3:63])[C:40](=[O:62])[C@H:41]([CH3:61])[NH:42][C:43](=[O:60])[C@H:44]([CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[NH:45][C:46](=[O:52])[O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:19])[CH3:16])[CH2:7][O:8][C:9]([CH3:10])([CH3:11])[CH3:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 117961541HCID 117961541, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 117735771HCID 117735771, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 178502594HCID 178502594, compoundCatalystHCID 887MethanolSolvent

Procedure

Hydroxypalladium/carbon (277 mg, 50% wet w/w) was added to a solution of benzyl (6S,9S,12S,18S,21S,24S,27S,30S)-30-(((S)-1-(((S)-1-((2-amino-2-oxoethyl)amino)-3-(tert-butoxy)-1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)(methyl)carbamoyl)-6,12,27-tribenzyl-18-isobutyl-24-isopropyl-2,2,9,11,21-pentamethyl-4,7,10,13,16,19,22,25,28-nonaoxo-3-oxa-5,8,11,14,17,20,23,26,29-nonaazadotriacontan-32-oate synthesized according to a conventional method (Boc-Phe-Ala-MePhe-Gly-Leu-Ala-Val-Phe-Asp(OBn)-MeAla-Ser(OtBu)-Gly-NH2) (Compound SP-506) (831 mg, 0.563 mmol) in methanol (5 ml)-ethyl acetate (5 ml) under a nitrogen atmosphere, the atmosphere was replaced with hydrogen, and the mixture was then stirred at room temperature for 3.5 hours. The reaction solution was then filtered through celite, and the filtrate was concentrated under reduced pressure to afford the title compound (SP-505) (648 mg, 83%).

Workup

  1. customsynthesized
  2. filtrationThe reaction solution was then filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-470568d541eb4340ae41d2624786fa5a
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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