HCID 71152421, compound → HCID 89315743, compound

HRID 1497288Notes

Reaction equation

HRID 1497288 reaction equation
[C:1]([O:9][C@@H:10]1[C@H:15]2[NH:16][C:17](=[O:19])[O:18][C@H:14]2[CH2:13][C@H:12]([CH2:20][OH:21])[C@H:11]1[O:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>[C:1]([O:9][C@@H:10]1[C@H:15]2[NH:16][C:17](=[O:19])[O:18][C@H:14]2[CH2:13][C@H:12]([CH:20]=[O:21])[C@H:11]1[O:22][C:23](=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 71152421HCID 71152421, compound

Product 1

HCID 89315743HCID 89315743, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (3 aS,4R,5R,6R,7aS)-6-(hydroxymethyl)-2-oxooctahydrobenzo[d]oxazole-4,5-diyl dibenzoate (1.76 g, 4.28 mmol) in dry DCM (40 mL) at 0° C. was added DMP (2.72 g, 6.42 mmol). The mixture was then stirred at room temperature for 4 h. The reaction was diluted with saturated aqueous NaHCO3 (20 mL) and 1 M Na2S2O3 (30 mL) and extracted with EtOAc (2×50 mL). The extracts were dried over MgSO4 and the solvents were evaporated to give (3aS,4R,5R,6S,7aS)-6-formyl-2-oxooctahydrobenzo[d]oxazole-4,5-diyl dibenzoate (1.75 g, 100%) which was carried onto next reaction without further purification. 1H NMR (400 MHz, CDCl3) δ 9.82 (s, 1H), 7.95 (d, J=7.8 Hz, 2H), 7.88 (d, J=7.8 Hz, 2H), 7.47-7.54 (m, 2H), 7.32-7.38 (m, 4H), 6.48 (s, 1H), 5.66 (t, J=8.2 Hz, 1H), 5.50 (dd, J=7.7 Hz, 5.8 Hz, 1H), 4.94-4.97 (m, 1H), 4.00 (t, J=6.6 Hz, 1H), 3.26-3.32 (m, 1H), 2.56 (dt, J=12.1 Hz, 2.5 Hz, 1H), 2.10-2.18 (m, 1H).

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. dry with materialThe extracts were dried over MgSO4
  3. customthe solvents were evaporated

Sources & evidence

ORD record
ord-0db1764e898e4465ad16bcd5dbceabe4
Source dataset
uspto-grants-2015_12
Patent number
US09199949B2

Reaction notes

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