HCID 82338196, compound → HCID 59592656, compound

HRID 2261104Notes

Reaction equation

HRID 2261104 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[CH3:12][O:13][C:14](=[O:29])[CH2:15][N:16]1[C:21]2[CH:22]=[C:23]([CH2:26][OH:27])[CH:24]=[CH:25][C:20]=2[O:19][CH2:18][C:17]1=[O:28]>C(Cl)Cl>[CH3:12][O:13][C:14](=[O:29])[CH2:15][N:16]1[C:21]2[CH:22]=[C:23]([CH:26]=[O:27])[CH:24]=[CH:25][C:20]=2[O:19][CH2:18][C:17]1=[O:28]

Participants

4

Reactant 2

HCID 82338196HCID 82338196, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 59592656HCID 59592656, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of PCC (4.2 g, 0.019 mol) and celite (4 g) in dry CH2Cl2 (100 mL) was cooled to 0° C. and slowly added a solution of methyl-[6-(hydroxymethyl)-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl]acetate (1.2 g, 0.0048 mol) in CH2Cl2 (30 mL) under N2. The reaction mixture was stirred at RT for 2 h, passed through celite, washed with CH2Cl2 (50 mL) and concentrated to give crude product, which was purified on silica gel affording 1.05 g (87%).

Workup

  1. washwashed with CH2Cl2 (50 mL)
  2. concentrationconcentrated
  3. customto give crude product, which
  4. customwas purified on silica gel affording 1.05 g (87%)

Sources & evidence

ORD record
ord-8b52a8d38cc447939789f9fbdc0606ec
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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