Triacetoxyperiodinane → HCID 10256500, compound

HRID 1796169Notes

Reaction equation

HRID 1796169 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:39])[C@@H:11]([NH:15][C:16](=[O:38])[CH:17]([CH2:27][C:28]1([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:30][CH2:29]1)[CH2:18][C:19]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[O:20])[CH2:12][CH2:13][CH3:14].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C@@H:11]([NH:15][C:16](=[O:38])[CH:17]([CH2:27][C:28]1([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:30][CH2:29]1)[CH2:18][C:19]([N:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)=[O:20])[CH2:12][CH2:13][CH3:14])=[O:39]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 69619127HCID 69619127, compound

Product 1

HCID 10256500HCID 10256500, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-[(S)-1-(Benzoxazol-2-yl-hydroxy-methyl)-butyl]-2-(1-benzyl-cyclopropylmethyl)-4-morpholin-4-yl-4-oxo-butyramide (55 mg, 0.103 mmol) in dry dichloromethane under N2 was added a solution of Dess-Martin Periodinane solution in dichloromethane (15% wt in DCM, 0.206 mmol) and stirred at room temperature for 1 hr. The mixture was quenched with a solution Na2SO3 (65.4 mg) in saturated NaHCO3 (20 mL). The aqueous layer was extracted with dichloromethane (2×25 mL). Organic extracts dried (MgSO4) and concentrated under reduced pressure. Residue purified by silica gel column chromatography eluting with a mixture of ethyl acetate and heptane (1:1 then 2:1) to give N-[(S)-1-(Benzoxazole-2-carbonyl)-butyl]-2-(1-benzyl-cyclopropylmethyl)-4-morpholin-4-yl-4-oxo-butyramide as white solid (43 mg).

Workup

  1. customThe mixture was quenched with a solution Na2SO3 (65.4 mg) in saturated NaHCO3 (20 mL)
  2. extractionThe aqueous layer was extracted with dichloromethane (2×25 mL)
  3. dry with materialOrganic extracts dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customResidue purified by silica gel column chromatography
  6. washeluting with a mixture of ethyl acetate and heptane (1:1

Sources & evidence

ORD record
ord-150e1e28af184cad9b15ae6fd3dc123f
Source dataset
uspto-grants-2006_04
Patent number
US07030116B2

Reaction notes

Loading…