Diisopropylethylamine → (S)-2-(2,6-dichloro-4-triisopropylsilanyloxy-benzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester

HRID 63739

Reaktionsgleichung

Reaktionsgleichung von HRID 63739
[CH2:1]([O:4][C:5](=[O:26])[C@@H:6]([NH2:25])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=2[CH3:20])=[CH:10][CH:9]=1)[CH2:2][CH3:3].[Cl:27][C:28]1[CH:36]=[C:35]([O:37][Si:38]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40])[CH:34]=[C:33]([Cl:48])[C:29]=1[C:30](O)=[O:31].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>>[CH2:1]([O:4][C:5](=[O:26])[C@@H:6]([NH:25][C:30](=[O:31])[C:29]1[C:28]([Cl:27])=[CH:36][C:35]([O:37][Si:38]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:43])[CH3:44])[CH:39]([CH3:40])[CH3:41])=[CH:34][C:33]=1[Cl:48])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=2[CH3:20])=[CH:12][CH:13]=1)[CH2:2][CH3:3]

Komponenten

5

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866913092,6-Dichloro-4-triisopropylsilanyloxybenzoic acidHCID 86691352(S)-2-amino-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester

Produkt 1

HCID 89721092(S)-2-(2,6-dichloro-4-triisopropylsilanyloxy-benzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester

Versuchsvorschrift

The title compound was prepared using a similar procedure as described in Example 1, Step 8, starting from (S)-2-amino-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester (3.95 g, 11 mmol), 2,6-dichloro-4-triisopropylsilanyloxy-benzoic acid (3.63 g, 10 mmol), HBTU (5.42 g, 14.3 mmol), and DIPEA (4.26 g, 5.75 mL, 33.0 mmol), and after ISCO column chromatography purification, resulted in an amorphous white solid (1.7 g, 24%). ES(+)-HRMS m/e calcd. for C35H47Cl2N3O6Si (M+H)+ 704.2684, obsd. 704.2683.

Aufarbeitung

  1. customafter ISCO column chromatography purification

Quellen und Nachweise

ORD-Eintrag
ord-4c92c9d476d74da8a695965c1b7477b6
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447035B2

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