(Benzylamino)acetaldehyde diethyl acetal → HCID 67448813, compound

HRID 2274671Notes

Reaction equation

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

Participants

Reactant 2

HCID 521961(Benzylamino)acetaldehyde diethyl acetal

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

Product 1

HCID 67448813HCID 67448813, compoundYield 43.5%

Procedure

According to the procedure described in the synthesis method of Compound III-1, N-benzyl-2,2-diethoxyethanamine (Compound IX-13) (43.3 g, 190 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=4:1) to obtain the title compound (55.0 g, 43%).

Workup

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

Sources & evidence

ORD record: ord-b22fded3077d443d9f992b23e3cc4d0b
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126981B2

Reaction notes

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