N-(2,2-Diethoxyethyl)pyridine-4-methylamine → HCID 67448593, compound

HRID 2361995Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:14][CH2:15][CH3:16])[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[CH3:2].[CH:17]1[C:29]2[CH:28]([CH2:30][O:31][C:32]([NH:34][C@@H:35]([CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[CH:42][CH:41]=3)[C:36](O)=[O:37])=[O:33])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[CH:20]=[CH:19][CH:18]=1>>[C:47]([O:46][C:43]1[CH:42]=[CH:41][C:40]([CH2:39][C@H:35]([NH:34][C:32](=[O:33])[O:31][CH2:30][CH:28]2[C:29]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[C:22]3[C:27]2=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:36]([N:6]([CH2:5][CH:4]([O:3][CH2:1][CH3:2])[O:14][CH2:15][CH3:16])[CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[O:37])=[CH:45][CH:44]=1)([CH3:50])([CH3:48])[CH3:49]

Participants

Reactant 2

HCID 96638N-(2,2-Diethoxyethyl)pyridine-4-methylamine2×

HCID 10895791Fmoc-L-Tyr(tBu)-OH

Product 1

HCID 67448593HCID 67448593, compoundYield 85.8%

Procedure

According to the procedure described in the synthesis method of Compound III-5, 2,2-diethoxy-N-(pyridin-4-ylmethyl)ethanamine (Compound IX-15) (70.8 g, 315 mmol) was coupled with (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-tert-butoxyphenyl)propanoic acid (128.6 g, 280 mmol) and the obtained residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=1:1 to 0:100) to obtain the title compound (160.0 g, 76%).

Workup

customthe obtained residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=1:1 to 0:100)

Sources & evidence

ORD record: ord-ce1f16cc95564f61921303b6b2da037f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691819B2

Reaction notes

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