HCID 86646786, compound → HCID 59544021, compound

HRID 2188805Notes

Reaction equation

HRID 2188805 reaction equation
[CH:1]([NH:3][C:4]1[CH:5]=[C:6]([CH:11]([OH:37])[CH2:12][NH:13][C@H:14]([CH3:36])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25]C(=O)OCC2C=CC=CC=2)[CH:7]=[CH:8][C:9]=1[OH:10])=[O:2].[H][H]>CO.[Pd]>[NH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]([NH:13][CH2:12][C@@H:11]([C:6]1[CH:7]=[CH:8][C:9]([OH:10])=[C:4]([NH:3][CH:1]=[O:2])[CH:5]=1)[OH:37])[CH3:36]

Participants

5

Reactant 2

HCID 86646786HCID 86646786, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59544021HCID 59544021, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of compound 23 (0.54 g, 1.05 mmol) dissolved in methanol (30 mL) and palladium catalyst (0.15 g, 10% Pd on carbon, 50% we) was stirred overnight at room temperature under one atmospheric hydrogen pressure. The catalyst was removed by filtration and washed with methanol (3×10 mL). The filtrate and washings were combined and concentrated under vacuum to complete dryness, affording the desired product 24 (0.40 g, 91% yield) as an off-white solid: 1H NMR (300 MHz, CD3OD) δ 1.31 (m, 15H), 1.48-1.58 (m, 4H), 1.75 (m, 2H), 260-2.80 (m, 5H), 4.66 (m, 1H), 5.09 (s, 2H), 6.82 (d, 1H), 7.00 (d, 1H), 8.02 (s, 1H), 8.30 (s, 1H); m/z (ESI) 380 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol (3×10 mL)
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dfef0a6a40e24e3a97b1991d840c88dd
Source dataset
uspto-grants-2012_12
Patent number
US08324218B2

Reaction notes

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