HCID 59784092, compound → HCID 59784098, compound

HRID 2079763Notes

Reaction equation

HRID 2079763 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:49])[C@@H:9]([CH3:48])[C:10]([NH:12][C@@H:13]([CH:45]([CH3:47])[CH3:46])[C:14]([N:16]1[CH2:21][CH2:20][N:19](C(OCC2C=CC=CC=2)=O)[CH2:18][C@H:17]1[C:32]([NH:34][C@H:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:38][CH2:37][CH2:36]1)=[O:33])=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[CH3:49][N:8]([C@@H:9]([CH3:48])[C:10]([NH:12][C@H:13]([C:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][C@H:17]1[C:32]([NH:34][C@H:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:38][CH2:37][CH2:36]1)=[O:33])=[O:15])[CH:45]([CH3:47])[CH3:46])=[O:11])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 59784092HCID 59784092, compound

Product 1

HCID 59784098HCID 59784098, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 6 (13.02 g, 19.2 mmol) is dissolved in MeOH (600 mL), to which is added 5% Pd/C (1.80 g). This mixture is stirred in a pressure vessel under an atmosphere of hydrogen (40 psi) for 2 h. The catalyst is then removed by filtration over celite and the solvent removed from the resulting filtrate to afford a crude oil which is purified by flash chromatography on silica gel (5% MeOH/CH2Cl2). The desired product 7 is obtained as a white foam (9.71 g, 93% yield): 1H NMR δ (CDCl3) 7.02-7.20 (m, 4H), 6.71 (br s, 1H), 6.37 (br d, J=8.8 Hz, 1H), 4.16-5.13 (br m, 4H), 3.10-3.71 (br m, 3H), 2.64-2.84 (br m, 7H), 1.58-2.11 (br m, 7H), 1.46 (s, 9H), 1.30 (d, J=7.1 Hz, 2H), 0.86-1.02 (br m, 3H), 0.75 (d, J=6.7 Hz, 2H), 0.53 (br d, J=6.7 Hz, 2H); LCMS (APCl+) 544.9 (MH+), 444.6 (MH+-BOC), 260.2 (MH+-dipeptide, 100%); HPLC (C8 column) 95.2%.

Workup

  1. customThe catalyst is then removed by filtration over celite
  2. customthe solvent removed from the resulting filtrate
  3. customto afford a crude oil which
  4. customis purified by flash chromatography on silica gel (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-016c8d1a2a554d589523a69168c9c21d
Source dataset
uspto-grants-2011_04
Patent number
US07932255B2

Reaction notes

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