1-Hydroxybenzotriazole → HCID 70570939, compound

HRID 2403566Notes

Reaction equation

HRID 2403566 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.[C:11]([O:15][C:16]([NH:18][CH2:19][C:20]([OH:22])=O)=[O:17])([CH3:14])([CH3:13])[CH3:12].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>ClC(Cl)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][N:9]([CH3:10])[C:20](=[O:22])[CH2:19][NH:18][C:16](=[O:17])[O:15][C:11]([CH3:12])([CH3:13])[CH3:14]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 457588Benzenemethanamine, 3-bromo-N-methyl-HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 70570939HCID 70570939, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1-(3-bromophenyl)-N-methylmethanamine (12.0 g) and N-(tert-butoxycarbonyl)glycine (11.5 g) in dichloroethane (80 ml) were added HOBt (9.7 g) and WSC hydrochloride (13.7 g), followed by stirring at room temperature overnight. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with CHCl3. The mixture was dried over Na2SO4 and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain tert-butyl {2-[(3-bromobenzyl)(methyl)amino]-2-oxoethyl}carbamate (21.3 g).

Workup

  1. extractionfollowed by extraction with CHCl3
  2. dry with materialThe mixture was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-3335095d0b6745a082190b57e0bd2c3e
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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