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Tributylamine → 1,1-Dimethylethyl N-[2-[[[7-(diethylamino)-2-oxo-2H-1-benzopyran-3-yl]carbonyl]amino]ethyl]carbamate

HRID 443320
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 443320
[CH2:1]([N:3]([CH2:18][CH3:19])[C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([C:15]([OH:17])=O)[C:10](=[O:14])[O:11]2)=[CH:6][CH:5]=1)[CH3:2].C(N(CCCC)CCCC)CCC.ClC(OCC(C)C)=O.[NH2:41][CH2:42][CH2:43][NH:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48]>CN(C=O)C.CCOC(C)=O>[C:47]([O:46][C:45]([NH:44][CH2:43][CH2:42][NH:41][C:15]([C:9]1[C:10](=[O:14])[O:11][C:12]2[C:7]([CH:8]=1)=[CH:6][CH:5]=[C:4]([N:3]([CH2:1][CH3:2])[CH2:18][CH3:19])[CH:13]=2)=[O:17])=[O:51])([CH3:50])([CH3:49])[CH3:48]
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Komponenten

7

Edukt 4

HCID 7622TributylamineHCID 62365Isobutyl chloroformateHCID 187201N-BOC-ethylenediamineHCID 6592947-Diethylaminocoumarin-3-carboxylic acid

Produkt 1

HCID 100241141,1-Dimethylethyl N-[2-[[[7-(diethylamino)-2-oxo-2H-1-benzopyran-3-yl]carbonyl]amino]ethyl]carbamateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

--A solution of 7-diethylaminocoumarin-3-carboxylic acid 2 (1.15 g, 5 mmol) and tri-n-butylamine (1.38 g, 7.5 mmol) in dry DMF (50 ml) was cooled in an ice bath and treated with isobutyl chloroformate (0.715 g, 5.2 mmol). The solution was stirred in the ice bath for 0.5 h, then a solution of the amine 3 (0.8 g, 5 mmol) in dry DMF (5 ml) was added. The mixture was allowed to warm to room temp. and kept for 3 h, then diluted with EtOAc and washed thoroughly with water, dilute aq. HCl, aq. NaHCO3 and water, dried and evaporated. The residue gave a yellow solid after trituration with a little ether. A portion (400 mg) was purified by flash chromatography to give the amide 4 as yellow prisms (0.345 g), m.p. 157-158° C. after crystallisation from EtOAc-light petroleum The remaining material crystallised without chromatography to give a further portion of the product (0.55 g, total yield 45%) (Found. C, 62.6;. H, 7.3; N, 10.4. C21H29N3O5 requires C, 62.5; H, 7.2; N, 10.4%); δH 8.95 (1 H, t, J 5.5, NH), 8.68 (1 H, s, 4-H), 7.42 (1 H, d, Jortho 8.8, 5-H) , 6.64 (1 H, dd, Jmeta 2.3, 6-H), 6.49 (1 H, d, 8-H), 5.08 (1 H, br S, NH), 3.23-3.64 (8 H, m, 4×CH2), 1.44 (9 H, S, CMe3) and 1.24 (6 H, t, J7, 2×Me).

Aufarbeitung

  1. temperatureto warm to room temp.
  2. washwashed thoroughly with water, dilute aq. HCl, aq. NaHCO3 and water
  3. customdried
  4. customevaporated
  5. customThe residue gave a yellow solid after trituration with a little ether
  6. customA portion (400 mg) was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c77e396022494d63a257bddbcb7a9f37
Quelldatensatz
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05898069

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