Sodium hydride → N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-hydroxy-2-propanamine

HRID 2209636Notes

Reaction equation

[C:1]([NH:20][CH:21]([CH2:24][OH:25])[CH2:22][OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[O:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]=[C:29]1[C:37]1[CH:44]=[CH:43][C:40]([CH2:41]Br)=[CH:39][CH:38]=1>C1COCC1.C(Cl)Cl>[C:1]([NH:20][CH:21]([CH2:22][OH:23])[CH2:24][O:25][CH2:41][C:40]1[CH:43]=[CH:44][C:37]([C:29]2[O:28][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[N:30]=2)=[CH:38][CH:39]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-trityl-1,3-dihydroxy-2-propanamine (3.7 g; 11 mmol) is dissolved in THF (22 ml) and cooled to 0° C. NaH (0.44 g; 11 mmol; 60% in oil) is added and the reaction is warmed to room temperature and allowed to stir for 2 hours. 4-(benzoxazol-2-yl)benzylbromide (1.6 g; 5.5 mmol) is added and the reaction allowed to stir for 15 hours. The reaction is diluted with CH2Cl2 and washed with H2O 2×, dried (Na2SO4), concentrated and purified by column chromatography with basic alumina and eluted with 2% MeOH/98% CH2Cl2 to obtain N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-hydroxy-2-propanamine as a white solid which is used directly in Step E.

Workup

temperaturethe reaction is warmed to room temperature
stirringto stir for 15 hours
washwashed with H2O 2×
dry with materialdried (Na2SO4)
concentrationconcentrated
custompurified by column chromatography with basic alumina
washeluted with 2% MeOH/98% CH2Cl2

Sources & evidence

ORD record: ord-0bbef601d63e45c788563e831381aea6
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05455260

Reaction notes

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