tert-Butyl bromoacetate → HCID 22479125, compound

HRID 2182604Notes

Reaction equation

HRID 2182604 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]23[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=4)[C:13](=[O:25])[N:12]2[CH2:11][CH2:10][NH:9][CH2:8]3)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Br[CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]>C1COCC1>[C:42]([O:41][C:39]([CH2:38][N:9]1[CH2:8][C:7]2([CH2:6][C:5]3[CH:26]=[CH:27][C:2]([Br:1])=[CH:3][CH:4]=3)[N:12]([C:13](=[O:25])[N:14]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)[C:15]2=[O:16])[CH2:11][CH2:10]1)=[O:40])([CH3:45])([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetate2×HCID 81531DiisopropylethylamineHCID 22479108HCID 22479108, compound

Product 1

HCID 22479125HCID 22479125, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(4-bromobenzyl)-8-(3,5-dichlorophenyl)-1,4,8-triazabicyclo[4.3.0]nonane-7,9-dione (0.11 g) in THF (5 mL) was added DIEA (0.1 mL) and tert-butyl bromoacetate (0.06 mL). Additional tert-butyl bromoacetate (0.040 mL) was added after 16 hours. After 40 hours, the reaction mixture was concentrated and the residue was diluted with EtOAc and washed with water, NaHCO3, and brine, dried (Na2SO4), filtered, and concentrated. Purification by chromatography (Silica gel: EtOAc/hexane: 1/5, Chromatotron) afforded the titled compound (0.124 g). MS (m/z) 582 (MH+). mp 74.7° C.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionthe residue was diluted with EtOAc
  3. washwashed with water, NaHCO3, and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography (Silica gel: EtOAc/hexane: 1/5, Chromatotron)

Sources & evidence

ORD record
ord-f1726f5a816e491681acec741201033f
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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