Triethylamine → HCID 12813314, compound

HRID 2413185Notes

Reaction equation

HRID 2413185 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[SH:29][CH2:30][C@@H:31]([CH3:42])[C:32]([N:34]1[C@H:38]([C:39]([OH:41])=[O:40])[CH2:37][S:36][CH2:35]1)=[O:33]>O1CCCC1.O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([S:29][CH2:30][C@@H:31]([CH3:42])[C:32]([N:34]2[C@H:38]([C:39]([OH:41])=[O:40])[CH2:37][S:36][CH2:35]2)=[O:33])=[O:11])=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 19266p-Acetamidobenzoic acidHCID 62365Isobutyl chloroformateHCID 171857YS 980

Product 1

HCID 12813314HCID 12813314, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

1.8 g of 4-acetylaminobenzoic acid is dissolved in 20 ml of dry tetrahydrofuran. To this solution, 1.4 ml of triethylamine is added. To this mixture, 1.3 ml of isobutyl chloroformate is added dropwise with stirring at -5° C. After ten minutes, to this solution, 20 ml of aqueous solution of 2.4 g of (4R)-3-[(2S)-3-mercapto-2-methylpropanoyl]-4-thiazolidinecarboxylic acid and 1.4 ml of triethylamine is added, and the mixture is stirred at room temperature for 30 min. To this reaction solution, 40 ml of water is added, and the obtained mixture is washed with ethyl acetate. The aqueous layer is acidified with conc. hydrochloric acid, and extracted with ethyl acetate. The organic layer is washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo to give oil, yield 4.1 g. The oil is purified by silica gel column chromatography to give the titled compound, yield 3.6 g (90%), mp. 206°-207° C. (methanol), [α]D27 -152.5° (c=1.0, methanol).

Workup

  1. waitAfter ten minutes
  2. stirringthe mixture is stirred at room temperature for 30 min
  3. washthe obtained mixture is washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give oil, yield 4.1 g
  9. customThe oil is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a618efcb44ac4645a880938411848cf2
Source dataset
uspto-grants-1985_01
Patent number
US04496578

Reaction notes

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