HCID 66861118, compound → HCID 66849329, compound

HRID 1161968Notes

Reaction equation

HRID 1161968 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH:20]([OH:30])[CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:14][CH:13]=1)(C)(C)C.[H][H]>[Pd].CO>[C:26]([O:25][C:23](=[O:24])[NH:22][CH2:21][CH:20]([OH:30])[CH2:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH2:7])=[CH:13][CH:14]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 2

HCID 66861118HCID 66861118, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66849329HCID 66849329, compoundYield 123.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 41 (0.8 g, 1.69 mmol) with 10% palladium on carbon (0.40 g, wet) in methanol (30 mL) was stirred for 3 h at room temperature under atmospheric pressure of hydrogen. The mixture was then filtered through a silica gel pad; the solvent was evaporated to provide 42 (0.705 g, 99%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.45 (s, 9H), 1.55 (m, 4H), 2.58 (m, 4H), 2.71 (m, 2H), 3.29 (m, 1H), 3.45 (m, 2H), 3.92 (m, 2H), 4.10 (br s, 1H), 5.10 (br s, 1H), 6.81 (d, 2H), 7.08 (d, 2H).

Workup

  1. filtrationThe mixture was then filtered through a silica gel pad
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-763dd1788d6b414b87933fc17525e92b
Source dataset
uspto-grants-2010_10
Patent number
US07820678B2

Reaction notes

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