L-Cysteine, methyl ester → Methyl 2-(4'-carboxy-4'-phthalimidobutyl)-4(R)-thiazolidinecarboxylate

HRID 543211

Reaktionsgleichung

Reaktionsgleichung von HRID 543211
[CH3:1][O:2][C:3](=[O:8])[C@H:4]([CH2:6][SH:7])[NH2:5].[CH:9]([CH2:11][CH2:12][CH2:13][C@H:14]([N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])[C:15]([OH:17])=[O:16])=O>O1CCCC1.C(Cl)(Cl)Cl>[C:15]([CH:14]([N:18]1[C:19](=[O:28])[C:20]2=[CH:27][CH:26]=[CH:25][CH:24]=[C:21]2[C:22]1=[O:23])[CH2:13][CH2:12][CH2:11][CH:9]1[NH:5][C@H:4]([C:3]([O:2][CH3:1])=[O:8])[CH2:6][S:7]1)([OH:17])=[O:16]

Komponenten

5

Edukt 2

HCID 29145L-Cysteine, methyl esterHCID 132416335-Formyl-2(S)-phthalimidopentanoic acid

Produkt 1

HCID 13241635Methyl 2-(4'-carboxy-4'-phthalimidobutyl)-4(R)-thiazolidinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of L-cysteine methyl ester (1.71 g) and 5-formyl-2(S)-phthalimidopentanoic acid (3.49 g) in 120 ml of tetrahydrofuran was stirred under nitrogen for 2.5 hours and then taken to dryness to yield a white foam. This residue was dissolved in 250 ml of chloroform and washed with water (2×30 ml). The combined aqueous layers were back extracted with chloroform (2×30 ml). The organic layers were dried (Na2SO4) and then concentrated in vacuo to give a white foam, 4.83 g. Tlc on silica [4:1 Ethyl acetate:acetic acid] indicated a major spot at Rf =0.72. Exact mass measurement showed a molecular ion at 392.1024 (calcd. 392.1041). 'H NMR spectrum (CDCl3) showed a multiplet at δ7.72 (4H) and a singlet at δ3.78(3H).

Aufarbeitung

  1. customto yield a white foam
  2. washwashed with water (2×30 ml)
  3. extractionThe combined aqueous layers were back extracted with chloroform (2×30 ml)
  4. dry with materialThe organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give a white foam, 4.83 g

Quellen und Nachweise

ORD-Eintrag
ord-cc8ebb0328564b33af8b92801d2c5b6c
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04661479

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