Sodium Thiosulfate → HCID 178457877, compound

HRID 2212251Notes

Reaction equation

HRID 2212251 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([OH:38])[CH:11]([NH:14][C:15](=[O:37])[CH:16]([NH:24][C:25](=[N:32][S:33]([CH3:36])(=[O:35])=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:12][CH3:13].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:11]([NH:14][C:15](=[O:37])[C@@H:16]([NH:24][C:25](=[N:32][S:33]([CH3:36])(=[O:35])=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[CH2:12][CH3:13])=[O:38]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 178457761HCID 178457761, compound

Product 1

HCID 178457877HCID 178457877, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-[1-(benzoxazol-2-yl-hydroxymethyl)propyl]-3-cyclohexyl-2-[(methanesulfonyliminophenylmethyl)amino]propionamide (250 mg, 0.463 mmol) in dry THF (10 mL) was added at room temperature Dess-Martin periodinane (265 mg, 0.626 mmol), and the mixture was stirred at the same temperature for 1 h. A 25% sodium thiosulfate solution (3 mL) and saturated sodium bicarbonate solution (3 mL) were added. The biphasic mixture was stirred for additional 30 min, diluted with ethyl acetate (30 mL), and washed with brine and then water. The organic extracts were were dried, concentrated in vacuo, and purified by flash chromatography on silica gel (eluted with 1:1 EtOAc/hexanes) to yield 188 mg (75%) of the title compound as a mixture of E/Z isomers in ca. 3.5:1 ratio. 1H NMR for a major isomer (400 MHz, CDCl3): δ 7.97–7.40 (9H, m), 6.96(1H, d, J=8.0 Hz), 6.11(1H, d, J=7.6 Hz), 5.71(1H, m), 4.81(1H, m), 3.07(s, 3H), 2.35–0.80(m, 15H), 1.13(3H, t, J=7.2 Hz). MS: 539.3(MH+).

Workup

  1. stirringThe biphasic mixture was stirred for additional 30 min
  2. washwashed with brine
  3. customThe organic extracts were were dried
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography on silica gel (eluted with 1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-e907b00f7f2447b39fd4b05b2094933c
Source dataset
uspto-grants-2006_09
Patent number
US07101880B2

Reaction notes

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