Ammonia → HCID 66621653, compound

HRID 415335Notes

Reaction equation

HRID 415335 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH3:33])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[O:21][C:22]3[C:28]([C:29]([O:31]C)=O)=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:34]>CO>[C:29]([C:28]1[C:22]2[O:21][C:20]([C:17]3[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][N:11]([CH3:33])[C:9](=[O:10])[O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:19][CH:18]=3)=[N:24][C:23]=2[CH:25]=[CH:26][CH:27]=1)(=[O:31])[NH2:34]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66621249HCID 66621249, compound

Product 1

HCID 66621653HCID 66621653, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(4-(2-((benzyloxycarbonyl)(methyl)amino)ethyl)phenyl)benzo[d]oxazole-7-carboxylate (150 mg, 0.34 mmol) was added to ammonia in methanol (5 ml) and the mixture was stirred at room temperature for 2 days. Evaporate the solvent to obtain benzyl 4-(7-carbamoylbenzo[d]oxazol-2-yl)phenethyl(methyl)carbamate as a white solid (140 mg, yield 96%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 2.84-2.91 (m, 5H), 3.52-3.56 (t, J=7 Hz, 2H), 4.96-5.05 (d, J=36 Hz, 2H), 7.28-7.42 (m, 6H), 7.47-7.51 (t, J=7.8 Hz, 2H), 7.80-7.82 (d, J=7.6 Hz, 1H), 7.85-7.87 (d, J=8 Hz, 2H), 7.94-7.96 (d, J=8 Hz, 1H), 8.18-8.2 (m, 2H); LC-MS (ESI) m/z: 430 (M+1)+.

Workup

  1. customEvaporate the solvent

Sources & evidence

ORD record
ord-af363cb7e3464781a29c61b6122760e9
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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