Water → HCID 86598330, compound

HRID 1393387Notes

Reaction equation

HRID 1393387 reaction equation
S(Cl)(C)(=O)=O.[CH2:6]([O:8][C:9](=[O:42])[C@H:10]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][C:31]=3[N:35]([CH2:39]CO)[CH2:36][CH2:37]O)[CH:26]=2)[CH:20]=1)[NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH3:7].O.[Cl-:44].[Li+].[CH2:46]([Cl:48])Cl>CO>[CH2:6]([O:8][C:9](=[O:42])[C@H:10]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][C:31]=3[N:35]([CH2:39][CH2:46][Cl:48])[CH2:36][CH2:37][Cl:44])[CH:26]=2)[CH:20]=1)[NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH3:7]

Participants

7

Reactant 5

HCID 962WaterHCID 6344Dichloromethane2×HCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 86598329HCID 86598329, compound

Product 1

HCID 86598330HCID 86598330, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of mesyl chloride (172 mg, 1.50 mmol) in methylene chloride (1 ml) was added to a solution of 3-[5-bis[2-(hydroxy)ethyl]amino-naphth-2-yl]-N-trifluoroacetyl-L-phenylalanine ethyl ester (268 mg, 0.50 mmol) in methylene chloride (9 ml) and the mixture was stirred at room temperature for 3 hrs. To the mixture was added water and the mixture was extracted with methylene chloride. The extract was washed with water and dried. The solvent was distilled off under reduced pressure. To the residue were added methanol (10 ml) and lithium chloride (638 mg, 15 mmol) and the mixture was stirred at room temperature for 1 hr. and heated under reflux for 5 hrs. After the mixture was cooled to room temperature, silica gel (3 g) was added thereto and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=5) to give 3-[5-bis[2-(chloro)ethyl]amino-naphth-2-yl]-N-trifluoroacetyl-L-phenylalanine ethyl ester (207 mg, 72%) as a pale yellow oil.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. distillationThe solvent was distilled off under reduced pressure
  5. stirringthe mixture was stirred at room temperature for 1 hr
  6. temperatureand heated
  7. temperatureunder reflux for 5 hrs
  8. temperatureAfter the mixture was cooled to room temperature
  9. additionsilica gel (3 g) was added
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=5)

Sources & evidence

ORD record
ord-4bf3ee524c7c4e9f87bbcf0ebdf8d0e4
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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