Tetrahydrofuran → HCID 18315377, compound

HRID 275843

Reaction equation

HRID 275843 reaction equation
O1CCCC1.CN(OC)[C:8](=[O:17])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH2:16].[C:20]([O:24][C:25]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1Br)=[O:26])([CH3:23])([CH3:22])[CH3:21].C([Li])CCC>C(OC(=O)C)C.O.CCCCCC>[NH2:16][C:10]1[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=1[C:8]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH2:28][NH:27][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])=[O:17]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 70183002-Bromo-N-(tert-butoxycarbonyl)benzylamineHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 18315377HCID 18315377, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,5-Trans-N-(2-fluorobenzyl)-5-(2-tert-butoxycarbonylaminomethylphenyl)-7-chloro-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetamide (1) A tetrahydrofuran (30 ml) solution of N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (4.3 g) and N-tert-butoxycarbonyl-2-bromobenzylamine (3.82 g) was cooled to −78° C. To the solution was gradually added dropwise a hexane solution of n-butyl lithium (1.6 mol/L) (42 ml). To the mixture were then added water (100 ml) and acetic acid ethyl ester (100 ml). The organic layer was washed with water and dried over anhydrous MgSO4. The solvent was then distilled off. The residual oily compound was purified by means of a silica gel column chromatography to give a yellow solid product, which was recrystallized from n-hexane-isopropyl ether. The crystals were collected by filtration to afford 2-amino-2′-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone (1.3 g) as a pale yellow crystalline product.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous MgSO4
  3. distillationThe solvent was then distilled off
  4. customThe residual oily compound was purified by means of a silica gel column chromatography
  5. customto give a yellow solid product, which
  6. customwas recrystallized from n-hexane-isopropyl ether
  7. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-e943361692b940519cd5f70b9d9b698f
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Linked notes

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