Hydrochloric Acid → HCID 86604860, compound

HRID 1431998Notes

Reaction equation

HRID 1431998 reaction equation
[NH2:1][C@H:2]([CH2:6][C:7]#[CH:8])[C:3]([OH:5])=[O:4].C([O-])([O-])=O.[Na+].[Na+].O.[Cl:16][C:17]1[CH:18]=[C:19]([S:24](Cl)(=[O:26])=[O:25])[CH:20]=[CH:21][C:22]=1[Cl:23].Cl.[Na+].[Cl-]>O.O1CCOCC1.CCOC(C)=O>[Cl:16][C:17]1[CH:18]=[C:19]([S:24]([NH:1][C@H:2]([CH2:6][C:7]#[CH:8])[C:3]([OH:5])=[O:4])(=[O:25])=[O:26])[CH:20]=[CH:21][C:22]=1[Cl:23]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 2735133Sodium Carbonate MonohydrateHCID 6992713D-Propargylglycine

Product 1

HCID 86604860HCID 86604860, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

(R)-2-Aminopent-4-ynoic acid (16.0 g, 141 mmol) and Na2CO3.H2O (36.8 g, 296 mmol) were dissolved in 500 mL H2O and 300 mL p-dioxane. To this solution was added 3,4-dichlorobenzene-1-sulfonyl chloride (33.0 g, 134 mmol) dropwise over 25 min. The solution was stirred at RT for 19 h. The solution was then acidified with 5N HCl to pH 1. EtOAc (400 mL) and sat'd NaCl aq. (200 mL) were added and organic layer was separated. The aqueous phase was extracted with EtOAc (200 mL×2), and the combined EtOAc extracts were washed with brine (400 mL×4) and dried over Na2SO4. The solvent was removed under reduced pressure and dried in vacuo to yield 38.

Workup

  1. additionwere added
  2. customorganic layer was separated
  3. extractionThe aqueous phase was extracted with EtOAc (200 mL×2)
  4. washthe combined EtOAc extracts were washed with brine (400 mL×4)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customdried in vacuo

Sources & evidence

ORD record
ord-f60cbc4a38a746399d55148764b0adea
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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