Sodium Thiosulfate → HCID 10239364, compound

HRID 1765688Notes

Reaction equation

HRID 1765688 reaction equation
[C:1]([C:5]1[N:9]=[C:8]([CH:10]([OH:35])[CH:11]([NH:14][C:15]([CH:17]([NH:26][C:27]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:28])[CH2:18][S:19]([CH2:22][CH:23]([CH3:25])[CH3:24])(=[O:21])=[O:20])=[O:16])[CH2:12][CH3:13])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[C:1]([C:5]1[N:9]=[C:8]([C:10]([CH:11]([NH:14][C:15]([CH:17]([NH:26][C:27]([N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)=[O:28])[CH2:18][S:19]([CH2:22][CH:23]([CH3:24])[CH3:25])(=[O:21])=[O:20])=[O:16])[CH2:12][CH3:13])=[O:35])[O:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 69756876HCID 69756876, compound

Product 1

HCID 10239364HCID 10239364, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Morpholine-4-carboxylic acid [1-{1-[(3-tert-butyl-1,2,4-oxadiazol-5-yl)-hydroxy-methyl]-propylcarbamoyl}-2-(2-methyl-propane-1-sulfonyl)-ethyl]-amide (0.271 g) was dissolved in dichloromethane (10 mL) and the Dess-Martin periodinane (0.424 g, 1 mmol) was added. The reaction mixture was stirred for two hours and then poured into a mixture of saturated sodium bicarbonate and saturated sodium thiosulfate solution (1/1, 50 mL). The phases were separated and the aqueous phase extracted with dichloromethane. The combined organic phases were washed with sodium bicarbonate solution and brine. The solution was dried with magnesium sulfate and then concentrated under vacuum. The residue was subjected to flash chromatography (gradient from 5% ethyl acetate in heptane to 75% ethyl acetate in heptane) to give morpholine-4-carboxylic acid [1-[1-(3-tert-butyl-1,2,4-oxadiazole-5-carbonyl)-propylcarbamoyl]2-(2-methyl-propane 1-sulfonyl)-ethyl]-amide, a mixture of diastereomers. 1H NMR (CDCl3, 300 MHz): [7.87 (d, J=6.5 Hz) 7.79 (d, J=7 Hz), 1H], [6.11 (d, J=6.5 Hz) 6.06 (d, J=6.5 Hz), 1H], 5.38–5.30 (m, 1H), 4.92–4.13 (m, 1H), 3.78–3.68 (m, 5H), 3.49–3.33 (m, 5H), 3.24–3.04 (m, 2H), 2.47–2.37 (m, 1H), 2.20–2.07 (m, 1H), 1.95–1.85 (m, 1H), 1.45 (s, 9H), 1.17 (d, J=6.5 Hz, 6H), [1.04 (t, J=7.5 Hz) 1.03 (t, J=7.5 Hz), 3H]. [LC/MS m/z=516 (M+H+)]

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase extracted with dichloromethane
  3. washThe combined organic phases were washed with sodium bicarbonate solution and brine
  4. dry with materialThe solution was dried with magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9cb57ffedefa41fa941700bbc085dfae
Source dataset
uspto-grants-2007_06
Patent number
US07226921B2

Reaction notes

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