HCID 53716603, compound → HCID 54311126, compound

HRID 351478Notes

Reaction equation

HRID 351478 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([CH:14]=[CH:15][C:16]([O:18][CH3:19])=[O:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C:10]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 53716603HCID 53716603, compound

Product 1

HCID 54311126HCID 54311126, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A methanolic solution of the compound of Example 201, Step A was hydrogenated (40 psi) in a Parr shaker over 10% Pd-C (35 mg). After 17 hours, the reaction was filtered through a pad of Celite® and then concentrated to give yellowish solid of the compound of the compound of Example 201, Step B (153 mg, 90%) which was a 1:2 mixture of ester and lactam: +APcl MS (M+1, ester)+ 363, (M+1, lactam)+ 331; 1H NMR (400 MHz, CDCl3) δ: 7.25-7.05 (arom, series of m, 5 H), 3.54 (ester Me, s 1H), 1.44 (lactam BOC, s, 6H), 1.37 (ester BOC, s, 3H).

Workup

  1. filtrationthe reaction was filtered through a pad of Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c94f9664ca524b0e8bfc81dea82d8ef5
Source dataset
uspto-grants-2004_06
Patent number
USRE038524E1

Reaction notes

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