Lithium Hydroxide → HCID 86649840, compound

HRID 2098260Notes

Reaction equation

HRID 2098260 reaction equation
[CH3:1][C:2]([CH3:68])([CH3:67])[O:3][C:4](=[O:66])[NH:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][C:12](=[O:65])[NH:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][C:20](=[O:64])[NH:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][C:28](=[O:63])[NH:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][C:36](=[O:62])[NH:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][C:44](=[O:61])[NH:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][C:52](=[O:60])[NH:53][CH2:54][C:55]([O:57]CC)=[O:56].[OH-].[Li+]>C1COCC1>[CH3:1][C:2]([CH3:68])([CH3:67])[O:3][C:4](=[O:66])[NH:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][C:12](=[O:65])[NH:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][C:20](=[O:64])[NH:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][C:28](=[O:63])[NH:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][C:36](=[O:62])[NH:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][C:44](=[O:61])[NH:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][C:52](=[O:60])[NH:53][CH2:54][C:55]([OH:57])=[O:56]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86649841HCID 86649841, compound2×

Product 1

HCID 86649840HCID 86649840, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 54,54-dimethyl-4,12,20,28,36,44,52-heptaoxo-5,8,13,16,21,24,29,32,37,40,45,48,53-tridecaoxa-3,11,19,27,35,43,51-heptaazapentapentacontan-1-oate (Compound 13, 2.4 g, 0.0025 mol) was dissolved in THF (30 mL) and then stirred. After slowly adding 2 N lithium hydroxide aqueous solution (8 mL), the mixture was stirred at room temperature for 40 minutes. After removing THF from the reaction mixture, 1 N HCl aqueous solution was slowly added for acidification. After extracting 3 times with dichloromethane, the organic layer was separated, dried with magnesium sulfate, and then concentrated. The target compound 54,54-dimethyl-4,12,20,28,36,44,52-heptaoxo-5,8,13,16,21,24,29,32,37,40,45,48,53-tridecaoxa-3,11,19,27,35,43,51-heptaaza-1-pentapentacontanoic acid (Compound 14, 2.3 g, 99.1%) was yielded.

Workup

  1. stirringthe mixture was stirred at room temperature for 40 minutes
  2. customAfter removing THF from the reaction mixture, 1 N HCl aqueous solution
  3. additionwas slowly added for acidification
  4. extractionAfter extracting 3 times with dichloromethane
  5. customthe organic layer was separated
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b94ff797237d43d0b53250dba7b69580
Source dataset
uspto-grants-2013_05
Patent number
US08450469B2

Reaction notes

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