Water ethanol → Sampatrilat

HRID 567939Notes

Reaction equation

HRID 567939 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:48]([OH:50])=[O:49])[CH2:27][C:28]1([C:33]([NH:35][C@H:36]([C:45]([OH:47])=[O:46])[CH2:37][C:38]2[CH:43]=[CH:42][C:41]([OH:44])=[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.C(O)C.O>[Pd].CC(C)=O>[C:48]([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:20])=[O:19])[CH2:27][C:28]1([C:33]([NH:35][C@H:36]([C:45]([OH:47])=[O:46])[CH2:37][C:38]2[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=2)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1)([OH:50])=[O:49]

Participants

5

Reactant 2

HCID 19096565Water ethanolHCID 86756336HCID 86756336, compound

Product 1

HCID 6324648Sampatrilat

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Procedure

A solution of (S,S,S)-N-(1-[3-(N6-benzyloxycarbonyl-N2-mesyllysylamino)-2-carboxypropyl]-1-cyclopentylcarbonyl)tyrosine (see Preparation 9) (371 g) in a 9:1 ethanol/water mixture (2.225 l) was hydrogenated at 414 kPa (60 psi) and room temperature over a 10% palladium-on-carbon catalyst (37.0 g) for 4 hours. The catalyst was filtered off and the filtrate evaporated to leave the crude product as a foam. This material was stirred with acetone (3.13 l) for 24 hours to give the title compound as a white amorphous solid (283 g). Found: C,52.97; H,7.02; N,8.97. C26H40N4O9S requires: C,53.41; H,6.90; N,9.58%.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated
  3. customto leave the crude product as a foam

Sources & evidence

ORD record
ord-e6b462697a0d4b07aa5dcf621a1306af
Source dataset
uspto-grants-2001_01
Patent number
US06180665B2

Reaction notes

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