HCID 67320466, compound → HCID 44544521, compound

HRID 1023000Notes

Reaction equation

HRID 1023000 reaction equation
C(OC([NH:11][CH2:12][CH2:13][S:14]([CH2:17][C@H:18]([NH:29][C:30]([NH:32][C@@H:33]1[CH2:48][C:47]2=[CH:49][CH:50]=[C:44]([CH:45]=[CH:46]2)[O:43][CH2:42][CH2:41][CH2:40][CH2:39][O:38][CH2:37][C@H:36]([CH:51]([CH3:53])[CH3:52])[NH:35][C:34]1=[O:54])=[O:31])[C:19]([O:21]CC1C=CC=CC=1)=[O:20])(=[O:16])=[O:15])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][CH2:12][CH2:13][S:14]([CH2:17][C@H:18]([NH:29][C:30]([NH:32][C@@H:33]1[CH2:48][C:47]2=[CH:46][CH:45]=[C:44]([CH:50]=[CH:49]2)[O:43][CH2:42][CH2:41][CH2:40][CH2:39][O:38][CH2:37][C@H:36]([CH:51]([CH3:52])[CH3:53])[NH:35][C:34]1=[O:54])=[O:31])[C:19]([OH:21])=[O:20])(=[O:16])=[O:15]

Participants

4

Reactant 1

HCID 67320466HCID 67320466, compound

Product 1

HCID 44544521HCID 44544521, compoundYield 16.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

83 mg of 5% palladium/C were added to a solution of 198 mg (0.26 mmol) of benzyl(R)-3-(2-benzyloxycarbonylaminoethanesulfonyl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-yl)ureido]propionate in 10 ml of methanol, and the mixture was hydrogenated under a hydrogen atmosphere (balloon pressure). After leaving to stand for 2 days, the mixture was filtered, concentrated and purified by preparative HPLC. The required fractions were combined and freeze dried after addition of 1N hydrochloric acid. 23 mg of the title compound were obtained as hydrochloride.

Workup

  1. customAfter leaving
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated
  4. custompurified by preparative HPLC
  5. customfreeze dried
  6. additionafter addition of 1N hydrochloric acid

Sources & evidence

ORD record
ord-2156c11ed39348208477a92b541e2bc8
Source dataset
uspto-grants-2014_05
Patent number
US08722655B2

Reaction notes

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