Isatoic Anhydride → HCID 55179411, compound

HRID 1663080Notes

Reaction equation

HRID 1663080 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[O:46]1[CH2:51][CH2:50][CH:49]([CH2:52]O)[CH2:48][CH2:47]1>C1COCC1>[O:46]1[CH2:51][CH2:50][CH:49]([CH2:52][N:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=3[C:2](=[O:3])[O:4][C:5]2=[O:12])[CH2:48][CH2:47]1

Participants

6

Reactant 4

HCID 8359Isatoic AnhydrideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2773573(Oxan-4-yl)methanol

Product 1

HCID 55179411HCID 55179411, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of isatoic anhydride (2.5 g) and triphenylphosphine (4.0 g) in THF (100 ml) at 0° C. was added drop-wise diisopropyl azodicarboxylate (3.0 ml), followed by addition (tetrahydro-pyran-4-yl)-methanol (1.78 g). The reaction mixture was stirred at room temperature for 15 hours, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (EtOAc/petroleum ether, 9/1) affording impure 1-(tetrahydro-pyran-4-ylmethyl)-1H-benzo[d][1,3]oxazine-2,4-dione. This material was treated with 27% sodium hydroxide (20 ml) at 50° C. for 48 hours. The mixture was cooled to room temperature and 37% hydrochloric acid (15 ml) was added. The mixture was extracted several times with EtOAc and the combined organic layers were washed with water, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica (EtOAc/petroleum ether, 2/8) and gave the title compound. 13C-NMR (DMSO-d6) δ 170.0, 151.0, 134.4, 131.6, 113.9, 111.2, 109.7, 66.7, 47.8, 34.1, 30.4.

Workup

  1. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-72915c8f9f1244b084a3f56066b2a30b
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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