Sodium hydride → HCID 68816339, compound

HRID 2104210Notes

Reaction equation

HRID 2104210 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@@H:11]([C:22]([OH:24])=[O:23])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[CH2:26][CH:27]1[CH2:30][CH2:29][CH2:28]1>CN(C)C=O>[C:3]([O:7][C:8]([NH:10][C@@H:11]([C:22]([OH:24])=[O:23])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:26][CH:27]2[CH2:30][CH2:29][CH2:28]2)[CH:14]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 111050N-((tert-Butoxy)carbonyl)-D-tryptophanHCID 2734658(Bromomethyl)cyclobutane

Product 1

HCID 68816339HCID 68816339, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 20 mL vial, NaH (60% in mineral oil) (0.092 g, 2.30 mmol) was added to a solution of N-(tert-butoxycarbonyl)-D-tryptophan (0.200 g, 0.657 mmol) in anhydrous N,N-dimethylformamide (4 mL) at 0° C. The reaction mixture was placed in a shaker for 20 min. at 0° C. (Bromomethyl)cyclobutane (0.074 mL, 0.657 mmol) was added to the solution and allowed to react for 10 hours at 0° C. The reaction mixture was quenched with H2O and acidified with 1M NaHSO4 until pH=3. The solution was extracted with CH2Cl2, washed with brine, dried over Na2SO4, and concentrated to give the title compound.

Workup

  1. customto react for 10 hours at 0° C
  2. customThe reaction mixture was quenched with H2O
  3. extractionThe solution was extracted with CH2Cl2
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-eca906a2424544a8ae686ec901241dbd
Source dataset
uspto-grants-2009_08
Patent number
US07576222B2

Reaction notes

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