Sodium hydride → [3-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-4-(propane-2-sulfonyl)-phenyl]-carbamic acid 2-(4-bromo-phenyl)-ethyl ester

HRID 735528Notes

Reaction equation

HRID 735528 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][OH:10])=[CH:6][CH:5]=1.C1([O:19][C:20](=O)[NH:21][C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH:31]([CH3:33])[CH3:32])(=[O:30])=[O:29])=[C:24]([CH2:34][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH3:36])[CH:23]=2)C=CC=CC=1>C1COCC1.O>[Br:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][O:10][C:20](=[O:19])[NH:21][C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH:31]([CH3:32])[CH3:33])(=[O:29])=[O:30])=[C:24]([CH2:34][N:35]([C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])[CH3:36])[CH:23]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 728512-(4-Bromophenyl)ethanolHCID 57842905[3-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-4-(propane-2-sulfonyl)-phenyl]-carbamic acid phenyl ester

Product 1

HCID 57842559[3-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-4-(propane-2-sulfonyl)-phenyl]-carbamic acid 2-(4-bromo-phenyl)-ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

Sodium hydride (60% in oil, 60 mg, 1.5 mmol) was added portionwise to a solution of 4-bromophenethyl alcohol (0.718 g, 3.57) in THF (6 mL) at 0° C. The reaction mixture was cooled to −40° C., and a solution of 16G (0.550 g, 1.19 mmol) in THF (5 mL) was added slowly dropwise. The reaction mixture was slowly warmed to 0° C., and then stirred for 3 h at 0° C. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (gradient from 0 to 50% ethyl acetate in hexanes) to give 16H (0.503 g, 74%) as a white solid.

Workup

  1. temperatureThe reaction mixture was slowly warmed to 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (gradient from 0 to 50% ethyl acetate in hexanes)
  7. customto give 16H (0.503 g, 74%) as a white solid

Sources & evidence

ORD record
ord-340e5c48d0ea4b0aad8c746cca7b261e
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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