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

HRID 735617Notes

Reaction equation

HRID 735617 reaction equation
[H-].[Na+].C1([O:9][C:10](=[O:34])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[C:14]([CH2:24][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH3:26])[CH:13]=2)C=CC=CC=1.[Br:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43]O)=[C:38]([CH2:45][CH3:46])[CH:37]=1>C1COCC1>[Br:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][O:9][C:10](=[O:34])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[C:14]([CH2:24][N:25]([C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])[CH3:26])[CH:13]=2)=[C:38]([CH2:45][CH3:46])[CH:37]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 578427842-(4-Bromo-2-ethylphenyl)ethanolHCID 57842905[3-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-4-(propane-2-sulfonyl)-phenyl]-carbamic acid phenyl ester

Product 1

HCID 57842899[3-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-4-(propane-2-sulfonyl)-phenyl]-carbamic acid 2-(4-bromo-2-ethyl-phenyl)-ethyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (190 mg, 4.7 mmol) was added in one portion to a solution of 16G (547 mg, 1.2 mmol) and 36B (1000 mg, 4.4 mmol) in THF (20 mL) at −40° C. The reaction was warmed slowly to ambient temperature over 2 h and stirred for 15 h. The reaction was quenched with saturated citric acid and diluted with EtOAc. The mixture washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes) to afford 43A (650 mg, 92%) as a yellow solid. MS (ESI) m/z 597.1/599.1 (M+H)+.

Workup

  1. customThe reaction was quenched with saturated citric acid
  2. additiondiluted with EtOAc
  3. washThe mixture washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9ab51c9227fd4cea910b3c912a424db7
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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