Diisopropylethylamine → 19-(1-tert-Butoxycarbonyl-3-{2-[2-(2-{2-[2-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)ethoxy]ethoxy}ethoxy)ethoxy]ethylcarbamoyl}propylcarbamoyl)nonadecanoic acid tert-butyl ester

HRID 1748239Notes

Reaction equation

HRID 1748239 reaction equation
[C:1]([O:5][C:6](=[O:58])[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:57])[NH:26][CH:27]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:28][CH2:29][C:30](=[O:49])[NH:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][C:46]([OH:48])=[O:47])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CN(C(O[N:72]1[C:77](=[O:78])[CH2:76][CH2:75][C:73]1=[O:74])=[N+](C)C)C.CCN(C(C)C)C(C)C>>[C:1]([O:5][C:6](=[O:58])[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:57])[NH:26][CH:27]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:28][CH2:29][C:30](=[O:49])[NH:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][C:46]([O:48][N:72]1[C:77](=[O:78])[CH2:76][CH2:75][C:73]1=[O:74])=[O:47])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 8727541919-{1-tert-Butoxycarbonyl-3-[2-(2-{2-[2-(2-carboxyethoxy)ethoxy]ethoxy}ethoxy)ethylcarbamoyl]propyl-carbamoyl}nonadecanoic acid tert-butyl ester

Product 1

HCID 8727540819-(1-tert-Butoxycarbonyl-3-{2-[2-(2-{2-[2-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)ethoxy]ethoxy}ethoxy)ethoxy]ethylcarbamoyl}propylcarbamoyl)nonadecanoic acid tert-butyl esterYield 157.7%

Procedure

19-{1-tert-Butoxycarbonyl-3-[2-(2-{2-[2-(2-carboxyethoxy)ethoxy]ethoxy}ethoxy)ethylcarbamoyl]propylcarbamoyl}nonadecanoic acid tert-butyl ester (0.68 g crude solution in THF 40 mL, 0.82 mmol) and TSTU (0.296 g, 0.982 mmol) were mixed, pH was adjusted by addition of DIPEA (0.171 mL) and the resulting mixture was stirred at RT overnight. This resulted in a clear solution which was evaporated to dryness and treated with diethylether, which afforded 1.2 g of the title compound as a waxy mass which was used without further purification.

Workup

  1. customThis resulted in a clear solution which
  2. customwas evaporated to dryness
  3. additiontreated with diethylether, which

Sources & evidence

ORD record
ord-8890868fd8644bda81d5c62fb5ce817e
Source dataset
uspto-grants-2015_10
Patent number
US09150633B2

Reaction notes

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