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

반응식

HRID 63739 반응식
[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]

참가 물질

5

반응물 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

생성물 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

실험 절차

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.

후처리

  1. customafter ISCO column chromatography purification

출처 및 근거

ORD 기록
ord-4c92c9d476d74da8a695965c1b7477b6
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447035B2

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