N-[N2-[[3-oxo-2-[(1-oxoheptyl)amino]-1-methyl-3-(phenylmethoxy)-propoxy]carbonyl]-N6-[(phenylmethoxy)carbonyl]-(R)-6-[(phenylmethoxy)carbonyl]-L-lysyl]-D-Alanine Phenylmethyl Ester → N-[(R)-6-carboxy-N2-[[2-carboxy-1-methyl-2-[(1-oxoheptyl)amino]ethoxy]carbonyl]-L-lysyl]-D-Alanine

HRID 1077959Notes

Reaction equation

HRID 1077959 reaction equation
C1(C[O:8][C:9](=[O:67])[C@@H:10]([CH3:66])[NH:11][C:12](=[O:65])[C@@H:13]([CH2:40][CH2:41][CH2:42][CH:43]([C:55]([O:57]CC2C=CC=CC=2)=[O:56])[NH:44]C(OCC2C=CC=CC=2)=O)[NH:14][C:15]([O:17][CH:18]([CH3:39])[CH:19]([NH:30][C:31](=[O:38])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:20](=[O:29])[O:21]CC2C=CC=CC=2)=[O:16])C=CC=CC=1>CCOC(C)=O.CCO.[OH-].[OH-].[Pd+2]>[C:55]([CH:43]([NH2:44])[CH2:42][CH2:41][CH2:40][C@H:13]([C:12]([NH:11][C@@H:10]([C:9]([OH:67])=[O:8])[CH3:66])=[O:65])[NH:14][C:15]([O:17][CH:18]([CH3:39])[CH:19]([C:20]([OH:29])=[O:21])[NH:30][C:31](=[O:38])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:16])([OH:57])=[O:56]

Participants

4

Reactant 1

HCID 86749716N-[N2-[[3-oxo-2-[(1-oxoheptyl)amino]-1-methyl-3-(phenylmethoxy)-propoxy]carbonyl]-N6-[(phenylmethoxy)carbonyl]-(R)-6-[(phenylmethoxy)carbonyl]-L-lysyl]-D-Alanine Phenylmethyl Ester

Product 1

HCID 86749717N-[(R)-6-carboxy-N2-[[2-carboxy-1-methyl-2-[(1-oxoheptyl)amino]ethoxy]carbonyl]-L-lysyl]-D-Alanine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of 1a-1 (140 mg, 0.15 mmol) in EtOAc/EtOH (5 mL:15 mL) is hydrogenated over Pd(OH)2 (Pearlman's catalyst, 20% on C, 100 mg) using a Parr apparatus at an initial pressure of 70 psi. After 5.5 h, filtration and evaporation gives a colorless glass. The latter is triturated with ether and the sides of the flask are scraped to provide a white crystalline powder. The ether solution is removed with a syringe and the solid is washed with two more portions of ether, dried, and characterized as 1a-11: NMR (CD3OD) δ 0.89 (m, 3 H), 1.22 (d, J=6.5, 3 H), 1.24-1.39 (m, 6 H), 1.42 (d, J=7.3, 3 H), 1.45-1.99 (m, 8 H), 2.26 (t, J≈7.5, 2H), 3.62 (m, 1 H), 4.06 (m, 1 H), 4.41 (m, 1 H), 4.89 (br s for OH, NH; one hidden CH signal), 5.14 (m, 1 H); MS (HR-FAB) m/z 519.2671 (M+H calcd. for C22H39N4O10, 519.2666).

Workup

  1. filtrationfiltration and evaporation
  2. customgives a colorless glass
  3. customThe latter is triturated with ether
  4. customto provide a white crystalline powder
  5. customThe ether solution is removed with a syringe
  6. washthe solid is washed with two more portions of ether
  7. customdried

Sources & evidence

ORD record
ord-f4b2573d8ab74f97879e1b31ee2efbbd
Source dataset
uspto-grants-1996_08
Patent number
US05545662

Reaction notes

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