HCID 21708984, compound → HCID 21709012, compound

HRID 651873Notes

Reaction equation

HRID 651873 reaction equation
C([O:8][C:9]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:12]2[N:13]([CH2:22][O:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH2:14][CH2:15][CH2:16][CH:17]([C:18]([O:20][CH3:21])=[O:19])[C:11]=2[CH:10]=1)C1C=CC=CC=1>[Pd]>[OH:8][C:9]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:12]2[N:13]([CH2:22][O:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH2:14][CH2:15][CH2:16][CH:17]([C:18]([O:20][CH3:21])=[O:19])[C:11]=2[CH:10]=1

Participants

3

Reactant 1

HCID 21708984HCID 21708984, compound

Product 1

HCID 21709012HCID 21709012, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Following the general procedure detailed for 85, 93 (0.028 g, 0.060 mmol, 1 equiv) was treated with 10% Pd—C (0.010 g, 0.009 mmol, 0.16 equiv) followed by aqueous HCO2NH4 (0.265 mL, 25% w/v, 18 equiv). Filtration and concentration gave 95 as an analytically pure white solid (0.0204 g, 0.0225 g theoretical, 91%): mp 113-115° C.; 1H NMR (500 MHz, CD3OD) major rotamer δ 8.25 (d, J=7.5 Hz, 1H), 8.14 (d, J=8.5 Hz, 1H), 7.55-7.45 (m, 2H), 6.60 (s, 1H), 4.41-4.33 (m, 4H), 3.66 (s, 3H), 2.85-2.79 (m, 1H), 2.64 (s, 3H), 2.35-2.20 (m, 1H), 2.13-1.95 (m, 1H), 1.71-1.67 (m, 2H); 13C NMR (125 MHz, CD3OD) major rotamer δ 157.2, 154.4, 140.9, 134.8, 128.3, 126.2, 125.8 (2C), 124.5, 124.3, 123.9, 72.5, 53.6, 49.9, 37.3, 36.9, 27.9, 25.5; IR (film) νmax 3283, 2938, 2857, 1672, 1621, 1591 cm31 1; FABHRMS (NBA-NaI) m/z 379.1081 (M+, C18H21NO6S requires 379.1090).

Workup

  1. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-90482b8856dc4424884eb05d76c61a8d
Source dataset
uspto-grants-2001_08
Patent number
US06281354B1

Reaction notes

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