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

HRID 37058Notes

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][S:14][CH2:13][C:12](=O)[NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[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][S: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-thia-4,7,10-triazacyclododecane-3,11-dione (0.352 g, 0.769 mmol) was dissolved in dry THF (10 ml) and cooled to 0° C. A 1M solution of borohydride -THF complex in THF (5 ml) was added under nitrogen and the mixture was stirred for 1 hour at ambient temperature and refluxed for 0.5 hours. To the cooled solution was added 2M hydrochloric acid (3 ml) and the resulting mixture was evaporated to dryness. Water (1 ml) and 25% ammonia solution (1 ml) was added and the mixture was extracted 3 times with 4 ml chloroform. The combined extracts were concentrated in vacuo and gave a yellow oil which showed absence of carbonyl bands in IR. Yield: 0.29 g (88%), FAB MS: 430(M+1).

Workup

temperaturerefluxed for 0.5 hours
customthe resulting mixture was evaporated to dryness
additionWater (1 ml) and 25% ammonia solution (1 ml) was added
extractionthe mixture was extracted 3 times with 4 ml chloroform
concentrationThe combined extracts were concentrated in vacuo
customgave a yellow oil which

Sources & evidence

ORD record: ord-6fdd10be6a49425ebe92f2a04d384fa3
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05419893

Reaction notes

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