Water → HCID 59687910, compound

HRID 562543Notes

Reaction equation

HRID 562543 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.O=C1CCC(=O)N1[O:19][C:20](=O)[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][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].O>CN1C(=O)CCC1>[C:38]([O:37][C:35]([CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:20]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1)=[O:19])=[O:36])([CH3:41])([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 962WaterHCID 655264-(Aminomethyl)Benzoic AcidHCID 595628071-tert-Butyl 16-(2,5-dioxopyrrolidin-1-yl) hexadecanedioate

Product 1

HCID 59687910HCID 59687910, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To 4-(Aminomethyl)benzoic acid (0.2 g, 1.32 mmol) was added in NMP (5 mL). Hexadecanedioic acid tert-butyl ester 2,5-dioxo-pyrrolidin-1-yl ester (0.58 g, 1.32 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was poured into water (100 mL), the precipitate was isolated by filtration and dried in vacuo. The crude material was recrystallized from toluene to give 4-[(15-tert-butoxycarbonylpentadecanoylamino)methyl]benzoic acid (413 mg).

Workup

  1. customthe precipitate was isolated by filtration
  2. customdried in vacuo
  3. customThe crude material was recrystallized from toluene

Sources & evidence

ORD record
ord-d3a1e6cf16e84016b65969a10e52caed
Source dataset
uspto-grants-2011_11
Patent number
US08067362B2

Reaction notes

Loading…