Hydrochloric Acid → HCID 22619641, compound

HRID 840507Notes

Reaction equation

HRID 840507 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.[OH-].[Na+].O=C1CCC(=O)N1[O:21][C:22](=O)[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:47]=[CH:46][C:30]2[CH:31]([CH2:40][CH2:41][CH2:42][N:43]([CH3:45])[CH3:44])[C:32]3[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=3[CH2:34][CH2:35][C:29]=2[CH:28]=1.Cl>O.C1COCC1>[CH3:45][N:43]([CH3:44])[CH2:42][CH2:41][CH2:40][CH:31]1[C:30]2[CH:46]=[CH:47][C:27]([O:26][CH2:25][CH2:24][CH2:23][C:22]([NH:1][CH2:2][C:3]3[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=3)=[O:21])=[CH:28][C:29]=2[CH2:35][CH2:34][C:33]2[CH:36]=[CH:37][CH:38]=[CH:39][C:32]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 655264-(Aminomethyl)Benzoic AcidHCID 86757925HCID 86757925, compound

Product 1

HCID 22619641HCID 22619641, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 32 mg (0.212 mmol) of 4-(aminomethyl)benzoic acid in 2 ml of H2O and 4 ml of THF was treated with approximately 0.1 ml of 2 N NaOH such that the pH of the mixture was about 9. This was then treated with a solution of 100 mg (0.209 mmol) of the TCA NHS ester 9 in 4.5 ml of THF. The pH was adjusted to about 8.5-9.0 with 2 N NaOH and the reaction was stirred at room temperature for 15 minutes. The reaction was neutralized to pH 6 with 2 N HCl, then extracted twice with CH2Cl2. The CH2Cl2 portions were combined, dried over anhydrous Na2SO4 and concentrated in vacuo to give 87 mg (81%) of the acid 15 as a pale yellow oil. This was used in the next step without further purification.

Workup

  1. extractionextracted twice with CH2Cl2
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-705e028b841d4081a6cbb237dd52ba98
Source dataset
uspto-grants-2002_04
Patent number
US06368814B1

Reaction notes

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