2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate → HCID 90000668, compound
Reaction equation
[C:1]([O:5][C:6](=[O:65])[C@@H:7]([NH:13][C:14](=[O:64])[CH2:15][CH2:16][C@@H:17]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[NH:18][C:19](=[O:56])[CH2:20][CH2:21][C@@H:22]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[NH:23][C:24](=[O:48])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CN(C(O[N:79]1[C:84](=[O:85])[CH2:83][CH2:82][C:80]1=[O:81])=[N+](C)C)C>>[O:81]=[C:80]1[CH2:82][CH2:83][C:84](=[O:85])[N:79]1[O:11][C:10](=[O:12])[CH2:9][CH2:8][C@H:7]([NH:13][C:14](=[O:64])[CH2:15][CH2:16][C@@H:17]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[NH:18][C:19](=[O:56])[CH2:20][CH2:21][C@@H:22]([C:49]([O:51][C:52]([CH3:53])([CH3:55])[CH3:54])=[O:50])[NH:23][C:24](=[O:48])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:42])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:65]Participants
3
Procedure
(S)-2-{(S)-4-tert-Butoxycarbonyl-4-[(S)-4-tert-butoxycarbonyl-4-(17-tert-butoxycarbonylheptadecanoylamino)butyrylamino]butyrylamino}pentanedioic acid 1-tert-butyl ester (2.8 g, 3.02 mmol) was activated with TSTU (1.0 g, 3.325 mmol) using the same method as described above, giving crude (S)-2-{(S)-4-tert-butoxycarbonyl-4-[(S)-4-tert-butoxycarbonyl-4-(17-tert-butoxycarbonylheptadecanoylamino)butyrylamino]butyrylamino}-pentanedioic acid 1-tert-butyl ester 5-(2,5-dioxopyrrolidin-1-yl)ester. LCMS (electrospray): m/z=1024 (M+1).
Sources & evidence
- ORD record
- ord-1fcdf5c2159f4baa862a265dd86c9a25
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045560B2
Reaction notes
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