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Triethylamine → (2R)-2-(4-Benzyloxyphenyl)-2-hydroxy-N-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide

HRID 1003279
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1003279
[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]([C@@H:13]([OH:17])[C:14]([OH:16])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.[NH2:21][C@H:22]1[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][C:26]([OH:32])=[CH:27][CH:28]=2)[CH2:23]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>ClCCl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:13]([OH:17])[C:14]([NH:21][C@H:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][C:26]([OH:32])=[CH:27][CH:28]=3)[CH2:23]2)=[O:16])=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 14010320(R)-2-(4-(benzyloxy)phenyl)-2-hydroxyacetic acidHCID 69543637(S)-2-amino-7-hydroxytetralin hydrobromide

Produkt 1

HCID 57141748(2R)-2-(4-Benzyloxyphenyl)-2-hydroxy-N-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide
Ausbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(R)-4-Benzyloxymandelic acid (2.43 g), (S)-2-amino-7-hydroxytetralin hydrobromide (2.87 g) and triethylamine (2.88 ml) were dissolved in dichloromethane (38 ml), and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (4.58 g) was added to the solution at room temperature with stirring. After reaction for 15 hours, ethyl acetate was added to the reaction mixture. The resulting mixture was washed with water, 1N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and brine successively, dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: chloroform/ethyl acetate=1/1) and following recrystallization from ethyl acetate-hexane gave (2R)-2-(4-benzyloxyphenyl)-2-hydroxy-N-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (3.48 g) having a melting point of 137-139° C.

Aufarbeitung

  1. customAfter reaction for 15 hours
  2. washThe resulting mixture was washed with water, 1N hydrochloric acid
  3. dry with materiala saturated aqueous sodium bicarbonate solution and brine successively, dried over anhydrous magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customPurification of the residue by medium pressure liquid column chromatography on silica gel (eluent: chloroform/ethyl acetate=1/1)
  6. customrecrystallization from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-fd31e8943b534a8884e08c6fb9654cf7
Quelldatensatz
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06046192

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