Diisopropylethylamine → HCID 131721993, compound

HRID 1953909Notes

Reaction equation

HRID 1953909 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.Br[CH:35]1[CH2:40][CH2:39][CH2:38][CH:37]=[CH:36]1.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]([CH:40]2[CH2:39][CH2:38][CH2:37][CH:36]=[CH:35]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 1370573-BromocyclohexeneHCID 53852269HCID 53852269, compound

Product 1

HCID 131721993HCID 131721993, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

4-Methyl-2-methylamino-pentanoic acid [2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-amide (Example 35) (1.0 mmol) was dissolved in THF (10 mL) and treated with 3-bromocyclohexene (1.5 mmol) and diisopropylethylamine (3 mmol). The reaction was stirred at 50° C. for 18 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 10-30% acetone/CH2Cl2 to give the title compound with the yields of 50%.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated to dryness
  3. customThe residue was chromatographed on silica gel eluting with a gradient of 10-30% acetone/CH2Cl2

Sources & evidence

ORD record
ord-2e0c0dffd2c24532a0761f984b655720
Source dataset
uspto-grants-2000_09
Patent number
US06117841

Reaction notes

Loading…