Diisopropylethylamine → HCID 23543159, compound

HRID 1953910Notes

Reaction equation

HRID 1953910 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:24][C:25](=[O:33])[CH:26]([NH:31][CH3:32])[CH2:27][CH:28]([CH3:30])[CH3:29])[C:17](=[O:23])[NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34]([C:38]1[CH:45]=[CH:44][C:41]([CH2:42]Br)=[CH:40][CH:39]=1)([CH3:37])([CH3:36])[CH3:35].C(N(C(C)C)CC)(C)C>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:24][C:25](=[O:33])[CH:26]([N:31]([CH2:42][C:41]2[CH:44]=[CH:45][C:38]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:39][CH:40]=2)[CH3:32])[CH2:27][CH:28]([CH3:29])[CH3:30])[C:17](=[O:23])[NH:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 53852269HCID 53852269, compound

Product 1

HCID 23543159HCID 23543159, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

2-(Methyl-amino)-4-methyl-pentanoic acid [2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-amide (0.5 mmol) was dissolved in THF (10 mL) and treated with 4-tert-butyl-benzyl bromide (0.75 mmol) and diisopropylethylamine (1.5 mmol). The reaction was stirred at 50° C. for 15 hours. Then the reaction mixture was allowed to cool to room temperature and concentrated to dryness. The residue was chromatographed on silica gel eluting with a gradient of 25% EtOAc/Hexanes to give the title compound with the yield of 40%.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated to dryness
  3. customThe residue was chromatographed on silica gel eluting with a gradient of 25% EtOAc/Hexanes

Sources & evidence

ORD record
ord-6396d0bacd6b44169ce8284f16c8f814
Source dataset
uspto-grants-2000_09
Patent number
US06117841

Reaction notes

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