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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-BOC-4-aminobenzoyl methionine methyl ester

HRID 1739128
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1739128
[C:1](NC1C=CC(C(O)=O)=CC=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:19][O:20][C:21](=[O:28])[C@H:22]([CH2:24][CH2:25][S:26][CH3:27])[NH2:23].CCN=C=N[CH2:34][CH2:35][CH2:36][N:37](C)C.[OH:40][C:41]1C2N=NNC=2[CH:44]=[CH:43][CH:42]=1>C(Cl)Cl.C(N(CC)CC)C>[CH3:19][O:20][C:21](=[O:28])[C@H:22]([CH2:24][CH2:25][S:26][CH3:27])[N:23]([C:41](=[O:40])[C:42]1[CH:34]=[CH:35][C:36]([NH2:37])=[CH:44][CH:43]=1)[C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27559314-{[(Tert-butoxy)carbonyl]amino}benzoic acidHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 67564255N-BOC-4-aminobenzoyl methionine methyl esterAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Into a dried, nitrogen filled flask was placed N-BOC-4-aminobenzoic acid (8.77 g, 36.97 mmol) in dry CH2Cl2 (148 ml) along with methionine methyl ester hydrochloride (8.12 g, 40.66 mmol). This solution was cooled in an ice bath and triethylamine (6.7 ml), EDCI (7.80 g, 40.66 mmol) and hydroxybenzotriazole (HOBT, 5.50 g, 40.66 mmol) were added. The mixture was stirred overnight, diluted with more CH2Cl2 and was extracted 3 times each with 1M HCl, 1M NaHCO3 and water. The CH2Cl2 was dried over MgSO4 and the solvent was removed in vacuo. The solid was recrystallized from ethyl acetate/ hexanes to yield 9.72 g (71.3%) of pure product. mp 184-185° C.; 1H NMR (CDCl3) 1.53 (9H, s), 2.06-2.18 (4H, m), 2.23-2.33 (1H, m), 2.59 (2H, t, J=7.6 Hz), 3.80 (3H, s), 4.92 (1H, m), 7.45 (2H, d, J=8.7 Hz), 7.77 (2H, d, J=8.7 Hz); 13C NMR (CDCl3) 15.59, 28.34, 30.15, 31.64, 52.10, 52.73, 81.20, 117.73, 127.8, 128.33, 141.88, 152.33, 166.50, 172.75; anal. calc. for C18H26N2O5S, C: 56.53, H: 6.85, N: 7.29; found, C: 56.47, H: 6.86, N: 7.29; m/ z (EI) 382 (M).

Aufarbeitung

  1. temperatureThis solution was cooled in an ice bath
  2. extractionwas extracted 3 times each with 1M HCl, 1M NaHCO3 and water
  3. dry with materialThe CH2Cl2 was dried over MgSO4
  4. customthe solvent was removed in vacuo
  5. customThe solid was recrystallized from ethyl acetate/ hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f7b68109e4f04f1a83b51e75fc329519
Quelldatensatz
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05965539

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