Acetonitrile → HCID 87307719, compound

HRID 2361845Notes

Reaction equation

HRID 2361845 reaction equation
C([O:5][C:6](=[O:54])[C@@H:7]([NH:13][C:14](=[O:53])[CH2:15][CH2:16][CH:17]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[NH:18][C:19](=[O:45])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][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][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])(C)(C)C.[B-](F)(F)(F)F.CN(C(O[N:68]1[C:73](=[O:74])[CH2:72][CH2:71][C:69]1=[O:70])=[N+](C)C)C.CCN([CH:81]([CH3:83])[CH3:82])C(C)C.[C:84](#N)C>>[O:70]=[C:69]1[CH2:71][CH2:72][C:73](=[O:74])[N:68]1[O:5][C:6](=[O:54])[C@@H:7]([NH:13][C:14](=[O:53])[CH2:15][CH2:16][CH:17]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[NH:18][C:19](=[O:45])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][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][C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])[CH2:8][CH2:9][C:10]([O:12][C:81]([CH3:83])([CH3:84])[CH3:82])=[O:11]

Participants

5

Reactant 4

HCID 6342Acetonitrile2×HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 87307836HCID 87307836, compound

Product 1

HCID 87307719HCID 87307719, compoundYield 54%

Procedure

To a solution of (S)-2-[4-tert-butoxycarbonyl-4-(19-tert-butoxycarbonylnonadecanoylamino)butyrylamino]pentanedioic acid 1-tert-butyl ester (2.81 g) in acetonitrile (80 ml) was added a solution of TSTU (1.32 g) in acetonitrile (20 ml). pH was adjusted to 8 with DIPEA. After stirring for 1.5 h the mixture was concentrated. The residue was recrystallized from acetonitrile to give the title compound (1.7 g, 54%).

Workup

  1. concentrationwas concentrated
  2. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-9a43f2666d1d4abc94696c1f0dc5b51f
Source dataset
uspto-grants-2014_04
Patent number
US08691759B2

Reaction notes

Loading…