Benzenebutanamine → (S)-2-Benzenesulfonylamino-3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-N-(4-phenylbutyl)-propionamide

HRID 660679Notes

Reaction equation

[C:1]1([S:7]([NH:10][C@@H:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][C:25](=[O:27])[N:24](CC[Si](C)(C)C)[S:23]3(=[O:35])=[O:34])=[C:18]([O:36]CC3C=CC=CC=3)[CH:17]=2)[C:12](O)=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:44]1([CH2:50][CH2:51][CH2:52][CH2:53][NH2:54])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[C:1]1([S:7]([NH:10][C@@H:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][C:25](=[O:27])[NH:24][S:23]3(=[O:34])=[O:35])=[C:18]([OH:36])[CH:17]=2)[C:12]([NH:54][CH2:53][CH2:52][CH2:51][CH2:50][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:13])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 83242Benzenebutanamine

HCID 68838051(S)-2-Benzenesulfonylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid

Product 1

HCID 57777360(S)-2-Benzenesulfonylamino-3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-N-(4-phenylbutyl)-propionamide

Procedure

The title compound is prepared from (S)-2-benzenesulfonylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid and 4-phenylbutylamine analogous to Example 210, steps C and D: (M−1)−=585. HPLC retention time: 1.27 min. (Method A).

Sources & evidence

ORD record: ord-74c85840df97480883311de24a88da29
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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