Diisopropylethylamine → HCID 87307836, compound

HRID 2169104Notes

Reaction equation

HRID 2169104 reaction equation
O=C1CCC(=O)N1[O:8][C:9](=O)[CH2:10][CH2:11][C@H:12]([NH:20][C:21](=[O:47])[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][CH2:38][CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[NH2:49][C@H:50]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:51][CH2:52][C:53](=[O:55])[OH:54].CCN(C(C)C)C(C)C>C1COCC1.O>[C:59]([O:58][C:56](=[O:57])[C@@H:50]([NH:49][C:9](=[O:8])[CH2:10][CH2:11][CH:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[NH:20][C:21](=[O:47])[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][CH2:38][CH2:39][C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])[CH2:51][CH2:52][C:53]([OH:54])=[O:55])([CH3:62])([CH3:61])[CH3:60]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1175051-(1,1-Dimethylethyl) hydrogen L-glutamateHCID 87307295HCID 87307295, compound

Product 1

HCID 87307836HCID 87307836, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-(19-tert-butoxycarbonylnonadecanoylamino)pentanedioic acid 1-tert-butyl ester 5-(2,5-dioxopyrrolidin-1-yl)ester (prepared similarly as described in WO 2005/012347) (4.1 g) in THF (100 ml) was added a solution of H-Glu-OtBu (1.47 g) in water (20 ml). pH was adjusted to 8 with DIPEA. The mixture was concentrated after stirring for 1.5 h. The residue was recrystallized from DCM to give the title compound as a white solid (2.81 g, 61%).

Workup

  1. concentrationThe mixture was concentrated
  2. customThe residue was recrystallized from DCM

Sources & evidence

ORD record
ord-fc5ee7b3c5eb4f63b95960712918d026
Source dataset
uspto-grants-2015_06
Patent number
US09045560B2

Reaction notes

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