6-Aminohexanoic Acid → HCID 15666021, compound

HRID 1756251Notes

Reaction equation

HRID 1756251 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OCC)=O.[NH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33]>>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 5646-Aminohexanoic AcidHCID 10928Ethyl chloroformateHCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acid

Product 1

HCID 15666021HCID 15666021, compound

Procedure

The second step was to activate the N-benzyloxycarbonyl-6-aminocaproic acid obtained by following the procedure of Example 3 A. above, with ethyl chloroformate followed by reaction with a second 6-aminocaproic acid linker to yield N-(N'-benzyloxycarbonyl-6-aminocaproyl)-6-aminocaproic acid. This second step was carried out as follows. A solution of 52.1 g (0.19M) of N-benzyloxycarbonyl-6-aminocaproic acid (thoroughly dried) dissolved in 640 mL of toluene and 20 mL of triethylamine, was cooled to between -5° to -10° C. in an isopropanol/dry ice bath before ethyl chloroformate (19.1 mL, 0.199M) was slowly added to give a white precipitate. The precipitate was removed by filtration and discarded. To the filtrate cooled in an ice-water bath there was added over 45 minutes a solution of 25.7 g (0.19M) of 6-aminocaproic acid in 100 mL of cold 2N NaOH. After stirring for 1 hr at 0° C. and then overnight at room temperature, the pH was adjusted to 8 with 6N NaOH and 1.2 L of H2O was added. The 1.3 L aqueous phase was washed with ethyl ether (3×200 mL), cooled in an ice bath, and acidified with concentrated HCL to give a white solid. The solid was filtered, thoroughly washed with water and stored in a desiccator. The partially dried solid was treated with 350 mL of hot ethyl acetate to give two layers. The ethyl acetate layer was dried (Na2SO4), filtered, concentrated to about 250 mL, and cooled to 4° C. to yield 19 g (27% yield) of N-(N'-benzyloxycarbonyl-6-aminocaproyl)-6-aminocaproic acid.

Workup

  1. customobtained

Sources & evidence

ORD record
ord-606f5c8ea46b4a32a4606e5b63cef713
Source dataset
uspto-grants-1995_08
Patent number
US05440023

Reaction notes

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