HCID 67822391, compound → HCID 67822702, compound

HRID 1032888Notes

Reaction equation

HRID 1032888 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:40]=[CH:41][CH:42]=1)[C:7]([C:9]1[CH:14]=[C:13]([CH2:15][N:16]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:12]([OH:27])=[C:11]([CH2:28][N:29]([CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:10]=1)=[O:8])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:40]=[CH:41][CH:42]=1)[C:7]([C:9]1[CH:10]=[C:11]([CH2:28][N:29]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH2:35][C:36]([O:38][CH3:39])=[O:37])[C:12]([OH:27])=[C:13]([CH2:15][N:16]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:14]=1)=[O:8]

Participants

4

Reactant 1

HCID 67822391HCID 67822391, compound

Product 1

HCID 67822702HCID 67822702, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 1 (0.89 g, 1.5 mmol) was stirred for 1 h in methanol (50 mL) with 10% Pd/C (90 mg) under hydrogen pressure of 50 psi. The mixture was filtered and evaporated in vacuo. The product was purified by chromatography on silica gel using light petroleum (b.p. 50°-70° C.)/ethyl acetate (2:5) as the eluent. The yield of yellowish oil was 0.40 g (48%). 1H NMR (CDCl3): k 3.56 (1H, s), 3.59 (8H, s), 3.71 (12H, s), 4.01 (6H, broad s), 7.05-7.14 (4H, m), 7.70 (2H, s).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated in vacuo
  3. customThe product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7688dcf3b84f4494bd801af6d7e68222
Source dataset
uspto-grants-1994_05
Patent number
US05308754

Reaction notes

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