Ammonia → HCID 18319595, compound

HRID 1699389Notes

Reaction equation

HRID 1699389 reaction equation
[C:1]([C:4]1[C:14]2[O:13][CH2:12][CH2:11][C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(O)=[O:2].O.O[N:22]1C2C=CC=CC=2N=N1.N>O1CCCC1>[C:1]([C:4]1[C:14]2[O:13][CH2:12][CH2:11][C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:2])[NH2:22]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 27960291-Hydroxybenzotriazole hydrateHCID 18319626HCID 18319626, compound

Product 1

HCID 18319595HCID 18319595, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 9-carboxy-2,3-dihydro-1-benzoxepin-4-carboxylate (1.0 g) in tetrahydrofuran (10 ml) was cooled in an ice bath. To this solution was added 1-hydroxybenzotriazole hydrate (0.57 g) and 1-(3-dimethylaminopropyl)-3-ethylcarboxiimide hydrochloride (0.80 g). Thereto aqueous ammonia (0.28 ml) was added dropwise at 5° C. The reaction mixture was stirred for 7 hours at ambient temperature and partitioned between ethyl acetate and 1N hydrochloric acid. The aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed successively with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of chloroform and methanol (9:1) to give ethyl 2,3-dihydro-9-carbamoyl-1-benzoxepin-4-carboxylate (0.31 g).

Workup

  1. custompartitioned between ethyl acetate and 1N hydrochloric acid
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washThe combined organic layer was washed successively with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of chloroform and methanol (9:1)

Sources & evidence

ORD record
ord-3ca952c3deac4e4c89a7c749ef072fe9
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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