Hydrochloric Acid → 5,9-Bis(benzyloxymethyl)-1-oxa-4,7,10-triazacyclododecane

HRID 1733791Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH:10]1[CH2:21][NH:20][CH2:19][CH:18]([CH2:22][O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[NH:17][C:16](=O)[CH2:15][O:14][CH2:13][C:12](=O)[NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1>[CH2:24]([O:23][CH2:22][CH:18]1[CH2:19][NH:20][CH2:21][CH:10]([CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[NH:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][NH:17]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5,9-Bis-(benzyloxymethyl)-1-oxa-4,7,10-triazacyclododecane-3,11-dione (0.250 g, 0.566 mmol) was dissolved in dry tetrahydrofuran (10 ml) cooled to 0° C. A 1M solution of borohydride-THF complex in tetrahydrofuran (5 ml) was added under nitrogen and the mixture was stirred at ambient temperature for 14 hours. 2M Hydrochloric acid (3 ml) was added and the mixture was concentrated in vacuo to approximately 1 ml volume. 25% Ammonia solution (2 ml) was added and the mixture was extracted four times with 4 ml of chloroform. The extracts were concentrated in vacuo and gave a yellow oil which showed an absence of carbonyl bands in IR. Yield 0.227 g (97%), FAB MS: 414 (M+1).

Workup

concentrationthe mixture was concentrated in vacuo to approximately 1 ml volume
addition25% Ammonia solution (2 ml) was added
extractionthe mixture was extracted four times with 4 ml of chloroform
concentrationThe extracts were concentrated in vacuo
customgave a yellow oil which

Sources & evidence

ORD record: ord-a32893798b614d1ca0bd40a25a4b6cb6
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05531978

Reaction notes

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