HCID 86666533, compound → HCID 14721696, compound

HRID 1397120Notes

Reaction equation

HRID 1397120 reaction equation
C([N:8]([C:13](=[O:35])[C@H:14]([CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:9][C:10]([OH:12])=[O:11])C1C=CC=CC=1>CO.[Pd]>[C:19]([O:18][C:16]([NH:15][C@H:14]([C:13]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[O:35])[CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])=[O:17])([CH3:20])([CH3:21])[CH3:22]

Participants

4

Reactant 1

HCID 86666533HCID 86666533, compound

Product 1

HCID 14721696HCID 14721696, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of benzyl ester 57 (1.09 g, 2.21 mmol) in MeOH (11 mL) was added palladium on carbon (10% wt, 100 mg) slurried in MeOH (1 mL). Hydrogen gas was bubbled through the solution to saturate, and the mixture was stirred under hydrogen atmosphere (balloon) for 1.5 h. The reaction mixture was filtered through celite, solids were rinsed with several small portions of MeOH. The combined filtrates were concentrated to dryness to provide acid 58 (887 mg, 99%) as a white foam. 1H NMR (400 MHz, DMSO-d6) δ 1.21-1.43 (m, 4H), 1.37 (2s, 18H), 1.43-1.53 (m, 1H), 1.55-1.63 (m, 1H), 2.84-2.90 (m, 2H), 3.68 (dd, J=17.6, 5.8 Hz, 1H), 3.78 (dd, J=17.6, 5.8 Hz, 1H), 3.87-3.92 (m, 1H), 6.74-6.77 (m, 1H), 6.82 (d, J=8.0 Hz, 1H), 8.03 (t, J=5.8 Hz, 1H).

Workup

  1. customHydrogen gas was bubbled through the solution
  2. concentrationto saturate
  3. filtrationThe reaction mixture was filtered through celite, solids
  4. washwere rinsed with several small portions of MeOH
  5. concentrationThe combined filtrates were concentrated to dryness

Sources & evidence

ORD record
ord-19f10caefc1d489f984da500f6657266
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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