HCID 86756335, compound → HCID 86756337, compound

HRID 567946Notes

Reaction equation

HRID 567946 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:22]([NH:24][CH2:25][C@@H:26]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:27][C:28]1([C:33]([NH:35][C@H:36]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[CH:40][CH:39]=2)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:23])[NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=O)C1C=CC=CC=1>[Pd]>[C:59]([O:58][C:56]([C@H:26]([CH2:25][NH:24][C:22](=[O:23])[C@H:16]([CH2:15][CH2:14][CH2:13][CH2:12][NH2:11])[NH:17][S:18]([CH3:21])(=[O:19])=[O:20])[CH2:27][C:28]1([C:33]([NH:35][C@H:36]([C:49]([O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[O:50])[CH2:37][C:38]2[CH:39]=[CH:40][C:41]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[CH:42][CH:43]=2)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:57])([CH3:60])([CH3:61])[CH3:62]

Participants

3

Reactant 1

HCID 86756335HCID 86756335, compound

Product 1

HCID 86756337HCID 86756337, compoundYield 112.8%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of tert-butyl (S,S,S)-N-(1-[3-(N6-benzyloxycarbonyl-N2-mesyllysylamino)-2-(tert-butoxycarbonyl)propyl]-1-cyclopentylcarbonyl)-O4-tert-butyltyrosinate (48.64 g, 54.8 mmmol) in industrial methylated spirits (1.0 L) was added 5% palladium-on-carbon (5 g) (water wet) and the mixture was hydrogenated at 345-414 kPa (50-60 psi) and at room temperature for 19 hours. After removal of the catalyst by filtration, the resulting solution was concentrated under reduced pressure to provide the title compound as a colourless oil (46.56 g) which contained ethanol.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. concentrationthe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e17582254481464aa0ea7cb39b0d21b8
Source dataset
uspto-grants-2001_01
Patent number
US06180665B2

Reaction notes

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