Fmoc-L-Tyr(tBu)-OH → HCID 131731294, compound

HRID 2361994Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:15][CH2:16][CH3:17])[CH2:5][NH:6][C@@H:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])[CH3:2].[CH:18]1[C:30]2[CH:29]([CH2:31][O:32][C:33]([NH:35][C@@H:36]([CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[CH:43][CH:42]=3)[C:37](O)=[O:38])=[O:34])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1>>[C:48]([O:47][C:44]1[CH:43]=[CH:42][C:41]([CH2:40][C@H:36]([NH:35][C:33](=[O:34])[O:32][CH2:31][CH:29]2[C:30]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=3[C:23]3[C:28]2=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:37]([N:6]([CH2:5][CH:4]([O:3][CH2:1][CH3:2])[O:15][CH2:16][CH3:17])[C@@H:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:8])=[O:38])=[CH:46][CH:45]=1)([CH3:51])([CH3:49])[CH3:50]

Participants

Reactant 2

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

HCID 37979251HCID 37979251, compound

Product 1

HCID 131731294HCID 131731294, compoundYield 87.7%

Procedure

According to the procedure described in the synthesis method of Compound III-5, (R)-2,2-diethoxy-N-(1-phenylethyl)ethanamine (Compound IX-14) (50.0 g, 210 mmol) was coupled with (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-tert-butoxyphenyl)propanoic acid (101.1 g, 220 mmol) and the obtained residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=4:1) to obtain the title compound (125.0 g, 87%).

Workup

customthe obtained residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-b9a2f384e71f4beba2e395f076565239
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691819B2

Reaction notes

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