Triethylamine → 1-[(S)-2-Hydroxy-1-oxopropyl]-L-proline, phenylmethyl ester

HRID 231936

Reaktionsgleichung

Reaktionsgleichung von HRID 231936
[C:1]([O-])(=[O:5])[CH:2]([CH3:4])[OH:3].[Na+].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.Cl.[NH:33]1[CH2:47][CH2:46][CH2:45][C@H:34]1[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36]>CN(C)C=O>[OH:3][C@@H:2]([CH3:4])[C:1]([N:33]1[CH2:47][CH2:46][CH2:45][C@H:34]1[C:35]([O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:36])=[O:5]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2733413Proline benzyl ester hydrochlorideHCID 23666456Sodium Lactate

Produkt 1

HCID 133352881-[(S)-2-Hydroxy-1-oxopropyl]-L-proline, phenylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of sodium lactate (1.7 g., 15.0 mmole), diphenylphosphorylazide (3.6 ml., 1.1 eq.), and dry dimethylformamide (30 ml.) at 0° (ice-bath) in an argon atmosphere is treated with triethylamine (2.1 ml., 1.0 eq.) and L-proline, phenylmethyl ester, monohydrochloride salt (3.6 g., 15.0 mmole). After 24 hours, the reaction mixture is partitioned between ethyl acetate and water. The aqueous phase is back extracted, the organic extracts are combined, washed with 5% potassium bisulfate, brine, and evaporated. The residue (5 g.) is chromatographed on silica (130 g.) eluting with (1:1, ethyl acetate/hexane) to give 2.5 g. of 1-[(S)-2-hydroxy-1-oxopropyl]-L-proline, phenylmethyl ester as a white crystalline solid after evaporation; m.p. 86°-88° (isopropyl ether). TLC (silica gel; ethyl acetate) Rf =0.4.

Aufarbeitung

  1. customthe reaction mixture is partitioned between ethyl acetate and water
  2. extractionThe aqueous phase is back extracted
  3. washwashed with 5% potassium bisulfate, brine
  4. customevaporated
  5. customThe residue (5 g.) is chromatographed on silica (130 g.)
  6. washeluting with (1:1, ethyl acetate/hexane)
  7. customto give 2.5 g
  8. customof 1-[(S)-2-hydroxy-1-oxopropyl]-L-proline, phenylmethyl ester as a white crystalline solid after evaporation

Quellen und Nachweise

ORD-Eintrag
ord-7a485f6d53ff404f95ed49cbab69faae
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04849414

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