1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 3(S)-(tert-butoxyformamido)-2(S)-hydroxy-N-(1(S)-phenylpropyl)heptanamide

HRID 635638

Reaktionsgleichung

Reaktionsgleichung von HRID 635638
O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:24]1([C@@H:30]([NH2:33])[CH2:31][CH3:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:34]([O:38][C:39]([NH:41][C@@H:42]([CH2:48][CH2:49][CH2:50][CH3:51])[C@H:43]([OH:47])[C:44](O)=[O:45])=[O:40])([CH3:37])([CH3:36])[CH3:35]>ClCCl>[C:34]([O:38][C:39]([NH:41][C@@H:42]([CH2:48][CH2:49][CH2:50][CH3:51])[C@H:43]([OH:47])[C:44]([NH:33][C@H:30]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:31][CH3:32])=[O:45])=[O:40])([CH3:37])([CH3:36])[CH3:35]

Komponenten

6

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6993773(1S)-1-phenylpropan-1-amineHCID 206399783(S)-(tert-butoxyformamido)-2(S)-hydroxyheptanoic acid

Produkt 1

HCID 206399793(S)-(tert-butoxyformamido)-2(S)-hydroxy-N-(1(S)-phenylpropyl)heptanamideAusbeute 75,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

229 mg of 1-hydroxybenzotriazole monohydrate, 287 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 148 mg of (S)-(−)-1-phenylpropylamine were added in sequence to a solution of 260 mg of 3(S)-(tert-butoxyformamido)-2(S)-hydroxyheptanoic acid in 10 ml of dichloromethane. The mixture was stirred at room temperature for 3 hours, then diluted with dichloromethane and washed in sequence with 5% citric acid solution, saturated sodium bicarbonate solution and saturated brine. The organic phase was dried over anhydrous magnesium sulphate and the solvent was evaporated to give 285 mg of 3(S)-(tert-butoxyformamido)-2(S)-hydroxy-N-(1(S)-phenylpropyl)heptanamide, MS: m/e 379.1 [M+H]+.

Aufarbeitung

  1. washwashed in sequence with 5% citric acid solution, saturated sodium bicarbonate solution and saturated brine
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  3. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b33c2eb908984462bba04a4ce2e61113
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06187905B1

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