Hydrochloric Acid → HCID 15500349, compound

HRID 583959Notes

Reaction equation

HRID 583959 reaction equation
[CH2:1]([C:18]([N+:31]([O-:33])=[O:32])([CH2:25][CH2:26][C:27]([O:29]C)=[O:28])[CH2:19][CH2:20][C:21]([O:23]C)=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[Li+].[OH-].Cl>COCCOC>[CH2:1]([C:18]([N+:31]([O-:33])=[O:32])([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 15500348HCID 15500348, compound

Product 1

HCID 15500349HCID 15500349, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Dimethyl 3-heptadecyl-3-nitropentane-1,5-dicarboxylate (7a) (138 mg, 0.29 mmol) was dissolved in DME (2 mL) and sat. aq LiOH solution (2 mL) was added. The mixture was let stand for 22 h, then it was acidified with dilute HCl (10%, 10 mL) and extracted with EtOAc (2×10 mL). The extracts were concentrated under a stream of dry N2 and the residue was subjected to flash column chromatography on silica (EtOAc/petroleum spirit, 15/85) to afford 3-heptadecyl-3-nitropentane-1,5-dicarboxylic acid (8a) (93 mg, 90%) as a white solid; mp 102° C.

Workup

  1. customfor 22 h
  2. extractionextracted with EtOAc (2×10 mL)
  3. concentrationThe extracts were concentrated under a stream of dry N2

Sources & evidence

ORD record
ord-b8897b282442497689257a5711bba407
Source dataset
uspto-grants-2005_08
Patent number
US06924309B2

Reaction notes

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