Water → HCID 59687910, compound

HRID 445003Notes

Reaction equation

HRID 445003 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 recrystalized 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 recrystalized from toluene

Sources & evidence

ORD record
ord-5ab31b71d78142d5b466c4c7cace2c19
Source dataset
uspto-grants-2013_07
Patent number
US08476228B2

Reaction notes

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