Diisopropylethylamine → HCID 87307702, compound

HRID 2169107Notes

Reaction equation

HRID 2169107 reaction equation
[C:1]([O:5][C:6](=[O:64])[CH:7]([NH:13][C:14](=[O:63])[CH2:15][CH2:16][CH:17]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[NH:18][C:19]([CH:21]1[CH2:26][CH2:25][CH:24]([CH2:27][NH:28][C:29](=[O:55])[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][CH2:46][CH2:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:23][CH2:22]1)=[O:20])[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:78]1[C:83](=[O:84])[CH2:82][CH2:81][C:79]1=[O:80])=[N+](C)C)C.CCN(C(C)C)C(C)C>C1COCC1>[O:80]=[C:79]1[CH2:81][CH2:82][C:83](=[O:84])[N:78]1[O:11][C:10](=[O:12])[CH2:9][CH2:8][CH:7]([NH:13][C:14](=[O:63])[CH2:15][CH2:16][CH:17]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[NH:18][C:19]([CH:21]1[CH2:26][CH2:25][CH:24]([CH2:27][NH:28][C:29](=[O:55])[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][CH2:46][CH2:47][C:48]([O:50][C:51]([CH3:52])([CH3:53])[CH3:54])=[O:49])[CH2:23][CH2:22]1)=[O:20])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:64]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 87307329HCID 87307329, compound

Product 1

HCID 87307702HCID 87307702, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[4-tert-butoxycarbonyl-4-({4-[(19-tert-butoxycarbonylnonadecanoylamino)methyl]-cyclohexanecarbonyl}amino)butyrylamino]pentanedioic acid 1-tert-butyl ester (4.6 g) in THF (150 ml) was added TSTU (1.68 g). DIPEA (0.97 ml) was added. After stirring over night the mixture was concentrated in vacuo. The residue was crystallized from acetonitrile to afford the title compound as a solid (4.4 g, 87%)

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-0520c2d6c016416294652fa88b50fdde
Source dataset
uspto-grants-2015_06
Patent number
US09045560B2

Reaction notes

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