Acetic Anhydride → (S)-N-(3-Chloro-2-hydroxypropyl)acetamide

HRID 1583083

Reaktionsgleichung

Reaktionsgleichung von HRID 1583083
C(N(CC)CC)C.Cl.[NH2:9][CH2:10][C@H:11]([OH:14])[CH2:12][Cl:13].[C:15](OC(=O)C)(=[O:17])[CH3:16]>C1COCC1>[C:15]([NH:9][CH2:10][C@H:11]([OH:14])[CH2:12][Cl:13])(=[O:17])[CH3:16]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1350101-Amino-3-chloro-2-propanol hydrochloride, (S)-

Produkt 1

HCID 11105542(S)-N-(3-Chloro-2-hydroxypropyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (10.5ml, 75.3 mmol, 1.11 eq) is added to a slurry of (S)-1-amino-3-chloro-2-propanol hydrochloride (V, EXAMPLE 1, 9,938 g, 68.059 mmol) in THF (80 ml) at −40° and the mixture stirred for 5 min at −40°. Acetic anhydride (6.78 ml, 71.86 mmol 1.056 eq) is then added at −40° and the mixture allowed to warm to 20-25° over 1.5 hrs. The precipitate is removed by filtration with reduced pressure and washed with THF. The filtrate is treated with magnesol (5.69 g), which is removed by filtration with reduced pressure and washed with THF (2×60 ml). The filtrate is then concentrated under reduced pressure. The concentrate is purified by flash chromatography (silica gel; eluting with a gradient of 75-100% ethyl acetate/cyclohexane) to give the title compound, NMR (CDCl3) 2.03, 3.32, 3.50-3.57, 3.55, 3.91-4.13, 5.01 and 7.09 δ; CMR (CDCl3) 23.00, 43.31, 46.52, 70.65 and 172.40 δ; MS (CI, NH3), M/Z (relative intensity), 171 (41.6), 169 (100), 154 (22.4), 152 (48.1); [α]25D=−7.44 (c=1.00, H2O).

Aufarbeitung

  1. temperatureto warm to 20-25° over 1.5 hrs
  2. customThe precipitate is removed by filtration with reduced pressure
  3. washwashed with THF
  4. additionThe filtrate is treated with magnesol (5.69 g), which
  5. customis removed by filtration with reduced pressure
  6. washwashed with THF (2×60 ml)
  7. concentrationThe filtrate is then concentrated under reduced pressure
  8. customThe concentrate is purified by flash chromatography (silica gel
  9. washeluting with a gradient of 75-100% ethyl acetate/cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-3191f845ecb9477a802dfda5f9a138b9
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06740754B2

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