Diisopropylethylamine → HCID 86631949, compound

HRID 906140Notes

Reaction equation

HRID 906140 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:16]=[C:15]([CH3:17])[C:11]([C:12]([OH:14])=[O:13])=[C:10]([NH:18][CH2:19][CH3:20])[C:9]=1[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.Cl[C:32](Cl)([O:34]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1>[CH2:19]([N:18]1[C:10]2[C:9]([CH3:21])=[C:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:16]=[C:15]([CH3:17])[C:11]=2[C:12](=[O:14])[O:13][C:32]1=[O:34])[CH3:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 86631948HCID 86631948, compound

Product 1

HCID 86631949HCID 86631949, compoundYield 253.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(tert-Butoxycarbonyl)-2-(ethylamino)-3,6-dimethylbenzoic acid (115 mg, 0.392 mmol) was dissolved in tetrahydrofuran (1 mL) and then cooled in an ice bath. N,N-Diisopropylethylamine (0.07 mL, 0.403 mmol) and triphosgene (40 mg, 0.135 mmol) were added, and the mixture was stirred at ambient temperature for 0.5 h. The mixture was quenched with water and extracted with dichloromethane (2×). The combined organic portion was dried over sodium sulfate, then filtered and concentrated to provide tert-butyl 1-ethyl-5,8-dimethyl-2,4-dioxo-2,4-dihydro-1H-benzo[d][1,3]oxazine-7-carboxylate (109 mg, 0.342 mmol, 87% yield). 1H NMR (400 MHz, CDCl3): δ 7.35 (s, 1H), 4.06 (q, 2H), 2.70 (s, 3H), 2.46 (s, 3H), 1.62 (s, 9H), 1.28 (t, 3H); MS (EI) for C17H21NO5: 320 (MH+).

Workup

  1. temperaturecooled in an ice bath
  2. customThe mixture was quenched with water
  3. extractionextracted with dichloromethane (2×)
  4. dry with materialThe combined organic portion was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-69a828d21a3c409688e598215ee055bc
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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