Benzyl chloroformate → HCID 70112251, compound

HRID 356218Notes

Reaction equation

HRID 356218 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:9][C:8](=[O:10])[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=2[NH:4]1.Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].C(=O)([O-])O.[Na+]>ClCCCl>[CH2:11]([N:7]1[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=2[NH:4][CH:3]([CH:2]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[NH2:1])[CH2:9][C:8]1=[O:10])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 18940551HCID 18940551, compound

Product 1

HCID 70112251HCID 70112251, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 4-(aminomethyl)-1-benzyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (0.99 g, 3.5 mmol) in 1,2-dichloroethane (15 mL) was cooled to 0° C., to which was added dropwise benzyl chloroformate (0.51 mL, 3.6 mmol). The mixture was stirred for 10 minutes at the same temperature, and for 25 minutes at room temperature. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate. The aqueous layer was separated, and the organic layer was washed with water and a saturated aqueous solution of sodium chloride, which was dried over magnesium sulfate, followed by filtration. The filtrate was concentrated under reduced pressure to give a crude product of l-benzyl-4-(benzyloxycarbonyl aminomethyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one. This crude product was dissolved in 1,2-dichloroethane (10 mL), to which was added phthalimidoacetyl chloride (0.79 g, 3.5 mmol). The mixture was stirred for 20 minutes at room temperature. To this solution was added 4-dimethylaminopyridine (DMAP) (43 mg, 0.35 mmol). The mixture was stirred for 25 minutes at room temperature, to which was further added DMAP (0.17 g, 1.4 mmol), and the mixture was stirred for 14 hours. To the reaction mixture was added water. The aqueous layer was separated. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, which was dried over magnesium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure. The concentrate was recrystallized from chloroform-petroleum ether to afford the end product (1.42 g, 67%). m.p.219°-221° C.

Workup

  1. waitfor 25 minutes at room temperature
  2. customThe aqueous layer was separated
  3. washthe organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, which was dried over magnesium sulfate
  5. filtrationfollowed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f68de29d3c944005826b8dc12b67a180
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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