Glycine, butyl ester, hydrochloride → HCID 66713729, compound

HRID 523809Notes

Reaction equation

HRID 523809 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([S:7][C:8]2[CH:9]=[C:10]([C:17]([OH:19])=O)[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=O)=[CH:3][CH:2]=1.Cl.[CH2:21]([O:25][C:26](=[O:29])[CH2:27][NH2:28])[CH2:22][CH2:23][CH3:24]>O>[CH2:21]([O:25][C:26](=[O:29])[CH2:27][N:28]1[C:17](=[O:19])[C:10]2[C:11](=[CH:15][CH:16]=[C:8]([S:7][C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[CH:9]=2)[C:12]1=[O:14])[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 83080Glycine, butyl ester, hydrochlorideHCID 66712961HCID 66712961, compound

Product 1

HCID 66713729HCID 66713729, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
250 °C

Procedure

A solid mixture of 4-(pyridin-4-ylsulfanyl)-phthalic acid (11.40 g) and glycine n-butyl ester hydrochloride salt (6.95 g) was heated in a oil bath (250° C.) with efficient stirring for 20 min. until the water bubble evaporation ceased. After cooling, it was partitioned between ethyl acetate (300 ml) and saturated sodium bicarbonate aqueous solution (150 ml). Two layers were separated and the aqueous layer was extracted with ethyl acetate (300 ml). Combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound 10.70 g. MS-(+)-ion: M+1=371.2.

Workup

  1. custombubble
  2. customevaporation
  3. temperatureAfter cooling
  4. customit was partitioned between ethyl acetate (300 ml) and saturated sodium bicarbonate aqueous solution (150 ml)
  5. customTwo layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (300 ml)
  7. washCombined organic layers were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-ceb6314a2b754f82a223c1334cf5f5a3
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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