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Sodium hydride → HCID 19757885, compound

HRID 1587533
Notes
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Reaction equation

HRID 1587533 reaction equation
[H-].[Na+].[C:3]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H].[C:30]([O:34][C:35]([N:37]([CH2:48][CH2:49][CH2:50][CH2:51]Cl)[S:38]([C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=1)(=[O:40])=[O:39])=[O:36])([CH3:33])([CH3:32])[CH3:31]>CN(C)C=O>[C:30]([O:34][C:35]([N:37]([S:38]([C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=1)(=[O:40])=[O:39])[CH2:48][CH2:49][CH2:50][CH2:51][N:19]([C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:11]([C:3](=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:51][CH2:50][CH2:49][CH2:48][N:37]([C:35]([O:34][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:36])[S:38]([C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=1)(=[O:40])=[O:39])=[O:36])([CH3:33])([CH3:32])[CH3:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 3475176HCID 3475176, compoundHCID 18962091HCID 18962091, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19757885HCID 19757885, compound

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
3×

Conditions

Temperature
0 °C

Procedure

Suspend sodium hydride (4.8 g, 0.2 mol) in anhydrous dimethylformamide (100 mL), cool to 0° C. and place under a nitrogen atmosphere. Add, by dropwise addition, a solution 1,9-bis(benzoyl)-1,9-diazanonane (33.8 g, 0.1 mol) in dimethylformamide. Stir until evolution of hydrogen ceases. Add, by dropwise addition, a solution of N-(tert-butyloxycarbonyl)-N-[(4-methylphenyl)sulfonyl]-4-chlorobutylamine (72.4 g, 0.2 mol) in dimethylformamide (100 mL). Stir overnight at room temperature then carefully quench with saturated ammonium chloride. Extract into ethyl acetate, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatogaphy to give the title compound.

Workup

  1. additionAdd, by dropwise addition
  2. additionAdd, by dropwise addition
  3. customthen carefully quench with saturated ammonium chloride
  4. extractionExtract into ethyl acetate
  5. dry with materialdry (MgSO4)
  6. customevaporate the solvent in vacuo
  7. customPurify by silica gel chromatogaphy

Sources & evidence

ORD record
ord-13dd396d4afc475694254f265ca65eca
Source dataset
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05217964

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes