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Triphenylphosphine → tert-butyl (3R,4R)-3-(4-tert-butoxy-benzoylamino)-4-(4-tert-butoxy-benzoyloxy)-azepan-1-carboxylate

HRID 895262
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 895262
[C:1]([O:5][C:6]1[CH:29]=[CH:28][C:9]([C:10]([NH:12][C@H:13]2[C@@H:19]([OH:20])[CH2:18][CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:14]2)=[O:11])=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[C:30]([O:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](O)=[O:40])=[CH:37][CH:36]=1)([CH3:33])([CH3:32])[CH3:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:1]([O:5][C:6]1[CH:29]=[CH:28][C:9]([C:10]([NH:12][C@H:13]2[C@H:19]([O:20][C:39](=[O:40])[C:38]3[CH:37]=[CH:36][C:35]([O:34][C:30]([CH3:32])([CH3:31])[CH3:33])=[CH:43][CH:42]=3)[CH2:18][CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:14]2)=[O:11])=[CH:8][CH:7]=1)([CH3:4])([CH3:2])[CH3:3]
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Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 5353024-tert-Butoxybenzoic AcidHCID 57267698tert-butyl (3R,4S)-3-(4-tert-butoxy-benzoylamino)-4-hydroxy-azepan-1-carboxylate

Produkt 1

HCID 53735547tert-butyl (3R,4R)-3-(4-tert-butoxy-benzoylamino)-4-(4-tert-butoxy-benzoyloxy)-azepan-1-carboxylateAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

262 mg of diethyl azadicarboxylate in 2 ml of tetrahydrofuran were added while stirring to 407 mg of the compound prepared in Example 16, 253 mg of 4-(tert-butoxy)-benzoic acid and 394 g of triphenylphosphine in 8 ml of tetrahydrofuran. After stirring at 50° C. for 4 hours, the solvent was removed under reduced pressure and the residue was taken up in 20 ml of cyclohexane and washed once with 20 ml of water and twice with 10 ml of 70% methanol/water each time. The aqueous-alcoholic phase was extracted twice with 10 ml of cyclohexane each time. The combined cyclohexane phases were dried over sodium sulphate and the solvent was removed under reduced pressure. The residual viscous oil was dissolved in 10 ml of hot heptane, seeded with pure end product and left to crystallize at room temperature for 18 hours and yielded 241 mg of tert-butyl (3R,4R)-3-(4-tert-butoxy-benzoylamino]-4-(4-tert-butoxy-benzoyloxy)-azepan-1-carboxylate of melting point 126-128° C. This compound can be reacted further as in Example 12b.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. washwashed once with 20 ml of water and twice with 10 ml of 70% methanol/water each time
  3. extractionThe aqueous-alcoholic phase was extracted twice with 10 ml of cyclohexane each time
  4. dry with materialThe combined cyclohexane phases were dried over sodium sulphate
  5. customthe solvent was removed under reduced pressure
  6. dissolutionThe residual viscous oil was dissolved in 10 ml of hot heptane
  7. waitleft
  8. customto crystallize at room temperature for 18 hours

Quellen und Nachweise

ORD-Eintrag
ord-3e2608f65b1e42dd9a00f9a700aa37e4
Quelldatensatz
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06914140B1

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