Sodium Sulfate → HCID 86585350, compound

HRID 1071080Notes

Reaction equation

HRID 1071080 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:29])[NH:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]=2[C:22]([CH3:28])([CH3:27])[CH:23]([OH:26])CO)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)=O.C(Cl)Cl.[O-]S([O-])(=O)=O.[Na+].[Na+]>O>[C:1]1([CH2:7][O:8][C:9](=[O:29])[NH:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]=2[C:22]([CH3:27])([CH3:28])[CH:23]=[O:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21584124Propan-2-one--dichloromethane (1/1)HCID 69795651HCID 69795651, compound

Product 1

HCID 86585350HCID 86585350, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (±)-N-[2-[2-(2,3-dihydroxy-1,1-dimethylpropyl)-1H-indol-3-yl]ethyl]-carbamic acid phenylmethyl ester (0.323 g, 0.81 mol) in 1:1 acetone/CH2Cl2 (19.5 mL) was added NaIO4 (0.350 g, 1.64 mmol) in H2O (2.2 mL). The reaction mixture was stirred for 3 h at rt. Solid Na2SO4 was added. The mixture was filtered. The filtrate was extracted with CH2Cl2. The CH2Cl2 extracts were dried, filtered, and concentrated to an oil. This oil was purified by silica chromatography to give the title compound: TLC Rf=0.31 (1:1 heptane/EtOAc); MS (ESI+) m/z 365.2; 1H NMR (300 MHz, CDCl3) δ 9.56 (1H), 8.11 (1H), 7.64 (1H), 7.37 (5H), 7.21 (1H), 7.13 (1H), 5.14 (2H), 4.92 (1H), 3.45 (2H), 2.95 (2H), 1.60 (6H).

Workup

  1. filtrationThe mixture was filtered
  2. extractionThe filtrate was extracted with CH2Cl2
  3. dry with materialThe CH2Cl2 extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customThis oil was purified by silica chromatography

Sources & evidence

ORD record
ord-eef3d3cc2fc545b2a65c76f35c485b0e
Source dataset
uspto-grants-2005_06
Patent number
US06903090B2

Reaction notes

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