HCID 58840906, compound → HCID 58840911, compound

HRID 1715070Notes

Reaction equation

HRID 1715070 reaction equation
[C:1]([O:5][C:6](=[O:37])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH:26]C(OCC1C=CC=CC=1)=O)[C:13](=[O:25])[NH:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.CO.[Pd]>[C:1]([O:5][C:6](=[O:37])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH2:26])[C:13](=[O:25])[NH:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 58840906HCID 58840906, compound

Product 1

HCID 58840911HCID 58840911, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of (7S)-7-benzyloxycarbonylamino-7-(quinolin-6-ylcarbamoyl)-heptanoic acid tert-butyl ester (11.0 g, 21.8 mmol) in EtOAc and MeOH was added 10% Pd/C. The reaction was charged with H2, degassed and refilled with hydrogen three times. The slurry was stirred at RT for 2 h at balloon pressure, then filtered through a plug of Celite, and solvent was removed under reduced pressure. The hydrogenolysis of the ester yielded 8.0 g (99%) of a thick oil solid after 19 h. 1H NMR (CDCl3) δ 8.9-7.3 (7H, m), 3.96 (1H, m), 2.31 (2H, t), 2.0-1.2 (17H, m). MS (ESI): (MH+) 372.2.

Workup

  1. additionThe reaction was charged with H2
  2. customdegassed
  3. additionrefilled with hydrogen three times
  4. filtrationfiltered through a plug of Celite, and solvent
  5. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-9a629340babf419cb85ac13cb7cffc9e
Source dataset
uspto-grants-2010_09
Patent number
US07799803B2

Reaction notes

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