Water → Benzyl 4-(4-carbamoylbenzo[d]oxazol-2-yl)benzyl(methyl)carbamate

HRID 415136Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[CH2:7]([O:14][C:15]([N:17]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:27][C:28]3[C:29](=[C:31]([C:35](O)=[O:36])[CH:32]=[CH:33][CH:34]=3)[N:30]=2)=[CH:22][CH:21]=1)[CH3:18])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH4+:38].[OH-].O>ClCCl>[C:35]([C:31]1[C:29]2[N:30]=[C:26]([C:23]3[CH:24]=[CH:25][C:20]([CH2:19][N:17]([CH3:18])[C:15](=[O:16])[O:14][CH2:7][C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)=[CH:21][CH:22]=3)[O:27][C:28]=2[CH:34]=[CH:33][CH:32]=1)(=[O:36])[NH2:38]

Participants

Conditions

Temperature: 50 °C

Procedure

Oxalyl chloride (218 mg, 1.72 mmol) is slowly added to a solution of 2-(4-(((benzyloxycarbonyl)(methyl)-amino)methyl)phenyl)benzo[d]oxazole-4-carboxylic acid (0.65 g, 1.57 mmol) in dichloromethane (10 mL) with stirring. The reaction mixture is warmed to 50° C. for 4 h and then cooled to 25° C. The solution is condensed in vacuum and then slowly added to 28% NH4OH (6 mL). The mixture is warmed to 50° C. and stirred for another 2 h. Water (50 mL) is added to the reaction mixture and the slurry is cooled to 25° C. The product is filtered and the cake is washed with water, dried to afford benzyl 4-(4-carbamoylbenzo[d]oxazol-2-yl)benzyl(methyl)carbamate solid. MS (ESI) m/e 416 [M+H]+.

Workup

temperaturecooled to 25° C
customcondensed in vacuum
temperatureThe mixture is warmed to 50° C.
stirringstirred for another 2 h
temperaturethe slurry is cooled to 25° C
filtrationThe product is filtered
washthe cake is washed with water
customdried

Sources & evidence

ORD record: ord-b42b0d50f7e2420886cb5161335fddd1
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088760B2

Reaction notes

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