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

HRID 415176

Reaction equation

HRID 415176 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[O:21][C:22]3[C:23](=[C:25]([C:29](O)=[O:30])[CH:26]=[CH:27][CH:28]=3)[N:24]=2)=[CH:16][CH:15]=1)[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=[N:38]C=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[Cl-].[NH4+].Cl>CN(C)C=O.O>[C:29]([C:25]1[C:23]2[N:24]=[C:20]([C:17]3[CH:18]=[CH:19][C:14]([CH2:13][N:11]([CH3:12])[C:9](=[O:10])[O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:15][CH:16]=3)[O:21][C:22]=2[CH:28]=[CH:27][CH:26]=1)(=[O:30])[NH2:38]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 666205582-(4-(((Benzyloxycarbonyl)(methyl)amino)methyl)phenyl)benzo[d]oxazole-4-carboxylic acid

Product 1

HCID 66621310Benzyl 4-(4-carbamoylbenzo[d]oxazol-2-yl)benzyl(methyl)carbamateYield 77.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(4-(((Benzyloxycarbonyl)(methyl)amino)methyl)phenyl)benzo[d]oxazole-4-carboxylic acid, (0.060 g, 0.14 mmol) in dimethyl formamide (10 mL) was added HOBT (0.025 g, 0.165 mmol), EDCI (0.035 g, 0.18 mmol), DIPEA (0.058 g, 0.45 mmol) and ammonium chloride (0.008 g, 0.15 mmol). The reaction mixture was stirred at room temperature for 20 hr, cooled and poured into water (10 mL). The pH was adjusted to 3 with 1N aqueous hydrochloric acid. The solution was extracted with dichloromethane (70 mL×3). The solution was washed with brine, dried, condensed in vacuum and separated by silica gel chromatography (ethyl acetate:methanol=1:0 to 10:1) to afford benzyl 4-(4-carbamoylbenzo[d]oxazol-2-yl)benzyl(methyl)carbamate 0.045 g solid (yield: 75.2%); LC-MS (ESI) m/z 416 [M+1]+.

Workup

  1. temperaturecooled
  2. extractionThe solution was extracted with dichloromethane (70 mL×3)
  3. washThe solution was washed with brine
  4. customdried
  5. customcondensed in vacuum
  6. customseparated by silica gel chromatography (ethyl acetate:methanol=1:0 to 10:1)

Sources & evidence

ORD record
ord-e7c06e315af64afd9ad7aa288d3e2afa
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Linked notes

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