Sodium Thiosulfate → HCID 10136465, compound

HRID 460413Notes

Reaction equation

HRID 460413 reaction equation
CC(OI1(O[C:20]([CH3:22])=[O:21])(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH:23]1([CH2:26][S:27]([CH2:30][C@H:31]([NH-:43])[C:32](=[O:42])[NH:33][CH:34]2[CH:39](O)[CH2:38][CH2:37][CH2:36][CH:35]2[OH:41])(=[O:29])=[O:28])[CH2:25][CH2:24]1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH:23]1([CH2:26][S:27]([CH2:30][C@H:31]([NH:43][C:32]([N:33]2[CH2:22][CH2:20][O:21][CH2:35][CH2:34]2)=[O:42])[C:32](=[O:42])[NH:33][C:34]2[C:35](=[O:41])[CH2:36][CH2:37][CH2:38][CH:39]=2)(=[O:28])=[O:29])[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 86594438HCID 86594438, compound

Product 1

HCID 10136465HCID 10136465, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dess Martin Periodinane (0.688 g, 1.62 mmol) was added to a solution of the [(R)-2-cyclopropylmethanesulfonyl-1-(2,6-dihydroxy-cyclohexylcarbamoyl)-ethyl]-amide (0.32 g) in DCM (10 mL) and the mixture was stirred at room temperature for 3 hours then treated with resin bound Na2S2O3 (1.5 mmol/g, 1.9 g) and stirred at room temperature for a further 24 hours. The reaction mixture was diluted with DCM (20 mL), then filtered. The filtrate was washed with a solution of 0.25 M Na2S2O3, then with saturated NaHCO3, then dried (MgSO4), and then evaporated under reduced pressure. The residue was subjected to column chromatography eluting with a mixture of ethyl acetate and heptane to give morpholine-4-carboxylic acid [(R)-2-cyclopropylmethanesulfonyl-1-(6-oxo-cyclohex-1-enylcarbamoyl)-ethyl]-amide. 1H NMR (CDCl3): 9.00 (s, 1H), 7.78 (t, 1H), 6.18 (d, 1H), 4.9 (m, 1H), 3.85 (m, 1H), 3.77–3.62 (m, 4H), 3.58–3.45 (dd, 1H), 3.48–3.36 (m, 4H), 3.0 (d, 2H), 2.55–2.42 (m, 4H), 2.08–1.97 (m, 2H), 1.2 (m, 1H), 0.8–0.7 (m, 2H), 0.6–0.4 (m, 2H). MS: 414 (MH+).

Workup

  1. additionthen treated with resin
  2. stirringstirred at room temperature for a further 24 hours
  3. filtrationfiltered
  4. washThe filtrate was washed with a solution of 0.25 M Na2S2O3
  5. dry with materialwith saturated NaHCO3, then dried (MgSO4)
  6. customevaporated under reduced pressure
  7. washeluting with a mixture of ethyl acetate and heptane

Sources & evidence

ORD record
ord-cbaa94db7409406dbbe51ef8195bab02
Source dataset
uspto-grants-2007_03
Patent number
US07196099B2

Reaction notes

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