Water → HCID 86756334, compound

HRID 567940Notes

Reaction equation

HRID 567940 reaction equation
C([O:8]C([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.O>C(OCC)(=O)C.[Pd]>[OH2:8].[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 962WaterHCID 86756336HCID 86756336, compound

Product 1

HCID 86756334HCID 86756334, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S,S,S)-N-(1-[3-(N6-benzyloxycarbonyl-N2-mesyllysylamino)-2-carboxypropyl]-1-cyclopentylcarbonyl)tyrosine (see Preparation 9) (351 g) in ethyl acetate (1300 ml) was added to water (385 ml) and the two phase mixture hydrogenated at 414 kPa (60 psi) and room temperature over a 5% palladium-on-carbon catalyst (35 g) for 20 hours. The catalyst was filtered off, the aqueous phase separated and concentrated to low volume under reduced pressure. The viscous solution was poured into methanol (2.85 l) and stirred at room temperature for 18 hours during which time there was a slow precipitation of a solid. The solid was granulated at 5-10° C. for 2 hours, filtered, washed with methanol and dried to give the title compound as a white solid (178.1 g), m.p. 168-171° C. Found: C,51.37; H,7.47; N,9.06. C26H40N4O9S.χH2O (where χ=1) requires: C,51.81; H,7.02; N,9.30%.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe aqueous phase separated
  3. concentrationconcentrated to low volume under reduced pressure
  4. additionThe viscous solution was poured into methanol (2.85 l)
  5. customa slow precipitation of a solid
  6. waitThe solid was granulated at 5-10° C. for 2 hours
  7. filtrationfiltered
  8. washwashed with methanol
  9. customdried

Sources & evidence

ORD record
ord-7d4153be13024888adf9f2e9d89677f9
Source dataset
uspto-grants-2001_01
Patent number
US06180665B2

Reaction notes

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