Trifluoroacetic acid → (S)-22-Carboxy-1-((2,5-dioxopyrrolidin-1-yl)oxy)-1,10,19,24-tetraoxo-3,6,12,15-tetraoxa-9,18,23-triazatritetracontan-43-oic acid

HRID 1632011Notes

Reaction equation

HRID 1632011 reaction equation
C([O:5][C:6](=[O:68])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](=[O:67])[NH:26][C@H:27]([C:60]([O:62]C(C)(C)C)=[O:61])[CH2:28][CH2:29][C:30](=[O:59])[NH:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][C:39](=[O:58])[NH:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH2:47][C:48]([O:50][N:51]1[C:55](=[O:56])[CH2:54][CH2:53][C:52]1=[O:57])=[O:49])(C)(C)C.C(O)(C(F)(F)F)=O>>[C:60]([C@@H:27]([NH:26][C:25]([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:68])=[O:5])=[O:67])[CH2:28][CH2:29][C:30](=[O:59])[NH:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][C:39](=[O:58])[NH:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH2:47][C:48]([O:50][N:51]1[C:55](=[O:56])[CH2:54][CH2:53][C:52]1=[O:57])=[O:49])([OH:62])=[O:61]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86644531C20-Otbu-glu(otbu)-aeea-aeea-osu

Product 1

HCID 58419214(S)-22-Carboxy-1-((2,5-dioxopyrrolidin-1-yl)oxy)-1,10,19,24-tetraoxo-3,6,12,15-tetraoxa-9,18,23-triazatritetracontan-43-oic acid

Procedure

Alternatively, the acylation reagent can be prepared employing a solid phase method to prepare the intermediate 19-((S)-1-tert-butoxycarbonyl-3-{2-[2-({2-[2-(2,5-dioxo-pyrrolidin-1-yloxycarbonylmethoxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethylcarbamoyl}propylcarbamoyl)nonadecanoic acid tert-butyl ester (alternative name: tBu-EicosanedioylgGlu(OtBu)-OEG-OEG-OH) as described in WO 2009/022005 followed by activation as Nhydroxysuccinimide ester and TFA cleavage (last two steps above).

Workup

  1. customAlternatively, the acylation reagent can be prepared

Sources & evidence

ORD record
ord-318b7f296ea540d193b00f8f164ce627
Source dataset
uspto-grants-2014_07
Patent number
US08791236B2

Reaction notes

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