Procysteine → HCID 53974988, compound

HRID 1250783Notes

Reaction equation

HRID 1250783 reaction equation
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][S:3]1.Cl.[CH3:11][O:12][C:13](=[O:20])[C@H:14]([CH2:16][CH:17]([CH3:19])[CH3:18])[NH2:15]>C1COCC1>[CH3:11][O:12][C:13](=[O:20])[C@H:14]([CH2:16][CH:17]([CH3:19])[CH3:18])[NH:15][C:7]([C@@H:5]1[CH2:4][S:3][C:2](=[O:1])[NH:6]1)=[O:9]

Participants

4

Reactant 2

HCID 72390ProcysteineHCID 2723695Leucine methyl ester hydrochloride

Product 1

HCID 53974988HCID 53974988, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (R)-(−)-2-oxo-thiazolidine-4-carboxylic acid (1.49 g, 10.2 mmols), L-Leucine methylester hydrochloride (1.85 g, 10.2 mmols) and N-methylmorpholinee (1.12 ml, 10.2 mmols) in anhydrous THF (15 ml), cooled at 0° C., was added, under stirring, a solution of DCDI (2.10 g, 10.2 mmols) and HBT (13 mg, 1 mmols) in anhydrous THF (8 ml). After standing one night at room temperature, the N,N′-dicyclohexylures and the hydrochloride of N-methylmorpholines were separated by filtration and the filtered substance was concentrated at reduced pressure. The product was purified by dilution of the raw reside with CHCl3 (50 ml) and extraction with saturated NaHCO3 solution (20 ml×2) and saturated NaCl solution (30 ml). Drying of the organic phase reunited on Na2SO4 and the removal of the solvent at reduced pressure provided the N-{[(R)-(2-Oxo-thiazolidine-4-yl)carbonyl]}-L-leucine methylester which was crystallized with EtOAc: 1.94 g (69%); m.p. 125-6° C.; [a]D22=−79° (1, methanol); IR (CHCl3): 3412, 2956, 1734, 1678, 1515, 1434, 1338, 1158 cm−1; 1H-NMR (CHCl3): d 0.90 and 0.95 [two s, 6, CH2CH(CH3)2], 1.42-74 [m, 3, CH2CH(CH3)2], 3.37-3.85 [m, 2, CH2S and 3.63 (s, 3, OCH3)], 4.18-4.69 (two m, 2, aCH and ring CH), 7.16 (d, 1, NH, J=8 Hz). Calculated for C11H17N2O4S: C, 48.34; H, 6.27; N, 10.25. Found C, 48.29; H, 6.80; N, 10.22%.

Workup

  1. additionwas added
  2. waitAfter standing one night at room temperature
  3. customthe N,N′-dicyclohexylures and the hydrochloride of N-methylmorpholines were separated by filtration
  4. concentrationthe filtered substance was concentrated at reduced pressure
  5. customThe product was purified by dilution of the raw reside
  6. extractionwith CHCl3 (50 ml) and extraction with saturated NaHCO3 solution (20 ml×2) and saturated NaCl solution (30 ml)
  7. customDrying of the organic phase
  8. customthe removal of the solvent at reduced pressure

Sources & evidence

ORD record
ord-94da97122fce43e289786762cc86258a
Source dataset
uspto-grants-2002_01
Patent number
US06339160B1

Reaction notes

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