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Water → (S)-2-{[1-(4-Chloro-1-naphthyl)-5-(2,6-dihydroxyphenyl)-3-pyrazolyl]carbonylamino}hexanoic acid

HRID 1682554
Notes
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Reaction equation

HRID 1682554 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[C:16]([C:17]3[C:22]([O:23]C)=[CH:21][CH:20]=[CH:19][C:18]=3[O:25]C)=[CH:15][C:14]([C:27]([NH:29][CH:30]([CH2:34][CH2:35][CH2:36][CH3:37])[C:31]([OH:33])=[O:32])=[O:28])=[N:13]2)=[CH:4][CH:3]=1.B(Br)(Br)Br.O.[OH-].[Na+]>ClCCl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[C:16]([C:17]3[C:18]([OH:25])=[CH:19][CH:20]=[CH:21][C:22]=3[OH:23])=[CH:15][C:14]([C:27]([NH:29][C@@H:30]([CH2:34][CH2:35][CH2:36][CH3:37])[C:31]([OH:33])=[O:32])=[O:28])=[N:13]2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 189266512-{[1-(4-Chloro-1-naphthyl)-5-(2,6-dimethoxyphenyl)-3-pyrazolyl]carbonylamino}hexanoic acid

Product 1

HCID 136008340(S)-2-{[1-(4-Chloro-1-naphthyl)-5-(2,6-dihydroxyphenyl)-3-pyrazolyl]carbonylamino}hexanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

0.3 g of 2-{[1-(4-chloro-1-naphthyl)-5-(2,6-dimethoxyphenyl)-3-pyrazolyl]carbonylamino}hexanoic acid is dissolved in 6.7 ml of dichloromethane and the mixture is cooled to -70° C. 5.7 ml of boron tribromide, dissolved in 20 ml of dichlormethane, are added dropwise and the reaction mixture is left for 2 hours at -70° C. It is allowed to return to room temperature, and 12 ml of water are then added while cooling. Concentrated NaOH is added to pH 14. The aqueous phase is washed with ether and brought to pH 2, the product is extracted with ethyl acetate and the organic phase is dried over sodium sulphate, filtered and evaporated. The residue is crystallised from diisopropyl ether.

Workup

  1. additionare added dropwise
  2. customto return to room temperature
  3. temperaturewhile cooling
  4. washThe aqueous phase is washed with ether
  5. extractionthe product is extracted with ethyl acetate
  6. dry with materialthe organic phase is dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is crystallised from diisopropyl ether

Sources & evidence

ORD record
ord-63eff1f561f249bca8ba9bd7cf38b2b4
Source dataset
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05635526

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes