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Water → HCID 19429707, compound

HRID 1078492
Notes
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Reaction equation

HRID 1078492 reaction equation
[H-].[Na+].[C:3]12([C:13]3[CH:14]=[C:15]([C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[CH:26]=[C:25]([C:30]([O:32][CH3:33])=[O:31])[CH:24]=[CH:23]5)[CH:16]=[CH:17][C:18]=3[OH:19])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[C:34]1([C:40]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[NH:41][CH2:42][CH2:43][CH2:44]Br)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O>CN(C=O)C>[C:3]12([C:13]3[CH:14]=[C:15]([C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[CH:26]=[C:25]([C:30]([O:32][CH3:33])=[O:31])[CH:24]=[CH:23]5)[CH:16]=[CH:17][C:18]=3[O:19][CH2:44][CH2:43][CH2:42][NH:41][C:40]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH2:10][CH:9]3[CH2:11][CH:5]([CH2:6][CH:7]([CH2:8]3)[CH2:12]1)[CH2:4]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2565813-Bromo-N-trityl-1-propanamineHCID 10136413HCID 10136413, compound

Product 1

HCID 19429707HCID 19429707, compound

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
3×

Procedure

360 mg (12 mmol) of sodium hydride (80% in oil) and 50 ml of DMF are introduced into a three-necked round-bottomed flask. A solution of 4.1 g (10 mmol) of methyl 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthoate in 75 ml of DMF are added dropwise, under a nitrogen stream, and the mixture is stirred until the evolution of gas ceases. A solution of 42 g (11 mmol) of N-triphenylmethyl-3-bromopropylamine in 50 ml of DMF is then introduced dropwise and the mixture is stirred at room temperature for 8 h. The reaction medium is poured into water, extracted with ethyl ether, the organic phase separated after settling has taken place, washed with water, dried over magnesium sulphate and evaporated. The residue obtained is purified by silica chromatography, eluted with a dichloromethane and hexane mixture (40-60). After evaporation of the solvents, 4.7 g (66%) of the expected product are recovered, which product melts at 168°-9° C.

Workup

  1. stirringthe mixture is stirred at room temperature for 8 h
  2. extractionextracted with ethyl ether
  3. customthe organic phase separated after settling
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by silica chromatography
  9. washeluted with a dichloromethane and hexane mixture (40-60)
  10. customAfter evaporation of the solvents, 4.7 g (66%) of the expected product
  11. customare recovered

Sources & evidence

ORD record
ord-2039bef32df54470b5895dc2c9dbcefd
Source dataset
uspto-grants-1996_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05547983

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes