Methyl chloroformate → HCID 69207609, compound

HRID 898159Notes

Reaction equation

HRID 898159 reaction equation
[NH2:1][C@H:2]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:3][CH2:4][N:5]1[CH2:24][CH2:23][C:8]2([NH:12][C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=3)[C:9]2=[O:22])[CH2:7][CH2:6]1.C(N(CC)CC)C.[Cl:38][C:39]([O:41][CH3:42])=[O:40]>ClCCCl>[ClH:38].[CH3:42][O:41][C:39](=[O:40])[NH:1][C@H:2]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][C:8]2([NH:12][C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=3)[C:9]2=[O:22])[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 11213585HCID 11213585, compound

Product 1

HCID 69207609HCID 69207609, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 8-(3-(S)-amino-3-phenylpropyl)-3-(4-bromobenzyl)-1,3,8-triaza-spiro[4.5]decane-2,4-dione (60 μmol) in anhydrous DCE (1 mL) was added triethylamine (10 μL, 72 μmol) and a solution of methyl chloroformate (72 μmol) in anhydrous DCE. The reaction mixture was agitated overnight at room temperature and then concentrated in vacuo. The residue was purified by semi-preparative HPLC (Method D) and lyophilized to give Compound 82 as a colorless solid (14.1 mg, 42%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by semi-preparative HPLC (Method D)

Sources & evidence

ORD record
ord-80557551ecad4f41a275c13563f298b7
Source dataset
uspto-grants-2008_04
Patent number
US07351713B2

Reaction notes

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