2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate → HCID 88946728, compound

HRID 2169115Notes

Reaction equation

HRID 2169115 reaction equation
[C:1]([O:5][C:6](=[O:78])[C@@H:7]([NH:13][C:14](=[O:77])[CH2:15][CH2:16][C@@H:17]([C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])[NH:18][C:19](=[O:69])[CH2:20][CH2:21][C@@H:22]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[NH:23][C:24](=[O:61])[CH2:25][CH2:26][C@@H:27]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[NH:28][C:29](=[O:53])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[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:92]1[C:97](=[O:98])[CH2:96][CH2:95][C:93]1=[O:94])=[N+](C)C)C>C(#N)C>[O:94]=[C:93]1[CH2:95][CH2:96][C:97](=[O:98])[N:92]1[O:11][C:10](=[O:12])[CH2:9][CH2:8][C@H:7]([NH:13][C:14](=[O:77])[CH2:15][CH2:16][C@@H:17]([C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])[NH:18][C:19](=[O:69])[CH2:20][CH2:21][C@@H:22]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[NH:23][C:24](=[O:61])[CH2:25][CH2:26][C@@H:27]([C:54]([O:56][C:57]([CH3:58])([CH3:59])[CH3:60])=[O:55])[NH:28][C:29](=[O:53])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:47])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:78]

Participants

4

Reactant 2

HCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 87307722HCID 87307722, compound

Product 1

HCID 88946728HCID 88946728, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-2-((S)-4-tert-Butoxycarbonyl-4-{(S)-4-tert-butoxycarbonyl-4-[(S)-4-tert-butoxycarbonyl-4-(17-tert-butoxycarbonylheptadecanoylamino)butyrylamino]butyrylamino}butyrylamino)pentanedioic acid 1-tert-butyl ester (0.1 g, 0.09 mmol) was activated with TSTU (29.8 mg, 0.099 mmol) in acetonitrile solution at RT for 1 h using the same method for activation and work up as described above. This afforded 100 mg crude activated product which could be used as such for insulin acylation without further purification. LC-MS (electrospray): m/z=1208 (M+1).

Workup

  1. customwithout further purification

Sources & evidence

ORD record
ord-7dab692ae4514e8aa89425f9a9890058
Source dataset
uspto-grants-2015_06
Patent number
US09045560B2

Reaction notes

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