Hydrochloric Acid → 5,9-Bis(benzyloxymethyl)-1-thia-4,7,10-triazacyclododecane
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]=1Participants
4
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 1 M 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 2 M 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-78d04cbecf3d4678b63b9ea780002738
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05198208
Reaction notes
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