6-Aminohexanoic Acid → HCID 57605522, compound

HRID 656352Notes

Reaction equation

HRID 656352 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].O=C1CCC(=O)N1[O:17][C:18](=O)[CH:19]([NH:27][C:28]([O:30][CH2:31][CH:32]1[C:44]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[C:38]2[C:33]1=[CH:34][CH:35]=[CH:36][CH:37]=2)=[O:29])[CH2:20][S:21][S:22][C:23]([CH3:26])([CH3:25])[CH3:24]>C([O-])(O)=O.[Na+].C1COCC1.CO.C(Cl)Cl>[C:23]([S:22][S:21][CH2:20][CH:19]([NH:27][C:28]([O:30][CH2:31][CH:32]1[C:44]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[C:38]2[C:33]1=[CH:34][CH:35]=[CH:36][CH:37]=2)=[O:29])[C:18]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:17])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 59718448HCID 59718448, compound

Product 1

HCID 57605522HCID 57605522, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 6-Aminohexanoic acid (0.158.g, 1.2 mmole) dissolved in 0.1M NaHCO3 (2.0 mL) was added the NHS ester 2 (0.68 g, 1.3 mmole) in 4 mL of anhydrous THF. The reaction mixture was stirred at RT for 2 hr. The solvent was completely evaporated and the dried solid residue obtained was dissolved in CH3OH/CH2Cl2 mixture and purified by silica gel column chromatography using 10% CH3OH/CH2Cl2 and obtained 3 as a white solid on evaporation the solvent. Yield: 0.5 g (77%).

Workup

  1. customThe solvent was completely evaporated
  2. customthe dried solid residue obtained
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-36ee43540f034a20a837038ec6123161
Source dataset
uspto-grants-2011_12
Patent number
US08071755B2

Reaction notes

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