1,2-Dichloroethane → HCID 10322491, compound

HRID 1796185Notes

Reaction equation

HRID 1796185 reaction equation
[CH3:1][C:2]1([CH2:7][CH:8]([CH2:12][C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])[C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:35][C@@H:36]([CH2:48][CH3:49])[CH:37]([C:39]1[O:40][C:41]2[C:42]([N:47]=1)=[N:43][CH:44]=[CH:45][CH:46]=2)[OH:38].CN1CCOCC1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(OCC)(=O)C.C([O-])(O)=O.[Na+].ClCCl>[CH3:1][C:2]1([CH2:7][CH:8]([CH2:12][C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])[C:9]([NH:35][CH:36]([C:37]([C:39]2[O:40][C:41]3[C:42]([N:47]=2)=[N:43][CH:44]=[CH:45][CH:46]=3)=[O:38])[CH2:48][CH3:49])=[O:11])[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

11

Reactant 7

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 24477Sodium ThiosulfateHCID 757711-HydroxybenzotriazoleHCID 159087TriacetoxyperiodinaneHCID 21025678HCID 21025678, compoundHCID 58697020HCID 58697020, compound

Product 1

HCID 10322491HCID 10322491, compoundYield 24.3%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-(1-Methyl-cyclopentylmethyl)-4-morpholin-4-yl-4-oxo-butyric acid (100 mg, 0.35 mmol) was combined with EDC (250 mg, 1.3 mmol), HOBt (250 mg, 1.6 mmol), and (2S)-2-amino-1-oxazolo[4,5-b]pyridin-2-yl-butan-1-ol (100 mg, 0.48 mmol). Dichloromethane (4 mL) was added and then 4-methylmorpholine (0.5 mL). The mixture was stirred at ambient temperature for 2 hours. After dilution with ethyl acetate (150 mL), the solution was washed with 1N aqueous HCl, water, saturated aqueous NaHCO3 solution and brine, dried with MgSO4 and evaporated under vacuum. The crude product was dissolved in dry dichloromethane (10 mL) and Dess-Martin Periodinane (500 mg, 1.2 mmol) was added. After stirring at ambient temperature for 1 hour, the mixture was diluted with ethyl acetate (150 mL) and treated with 0.26M Na2S2O3 solution in saturated aqueous NaHCO3. The organic phase was washed with saturated aqueous NaHCO3 and brine, dried with MgSO4 and evaporated. The product was purified by flash chromatography on silica gel (hexane/ethyl acetate 1:1) to yield the title compound (40 mg; 0.085 mmol) as a mixture of diastereomers.

Workup

  1. washAfter dilution with ethyl acetate (150 mL), the solution was washed with 1N aqueous HCl, water, saturated aqueous NaHCO3 solution and brine
  2. dry with materialdried with MgSO4
  3. customevaporated under vacuum
  4. dissolutionThe crude product was dissolved in dry dichloromethane (10 mL)
  5. stirringAfter stirring at ambient temperature for 1 hour
  6. washThe organic phase was washed with saturated aqueous NaHCO3 and brine
  7. dry with materialdried with MgSO4
  8. customevaporated
  9. customThe product was purified by flash chromatography on silica gel (hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-8b1add3da6234daf81f95749fd2313af
Source dataset
uspto-grants-2006_04
Patent number
US07030116B2

Reaction notes

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