Azane;hydrate → Benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)azetidine-1-carboxylate

HRID 415260Notes

Reaction equation

HRID 415260 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15]2[O:16][C:17]3[C:23]([C:24]([O:26]C)=O)=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH3:29]>>[C:24]([C:23]1[C:17]2[O:16][C:15]([CH:13]3[CH2:14][N:11]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])[CH2:12]3)=[N:19][C:18]=2[CH:20]=[CH:21][CH:22]=1)(=[O:26])[NH2:29]

Participants

3

Reactant 2

HCID 12896473Azane;hydrateHCID 66621079Methyl 2-(1-(benzyloxycarbonyl)azetidin-3-yl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 66621201Benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)azetidine-1-carboxylateYield 60%

Conditions

Temperature
35 °C

Procedure

Methyl 2-(1-(benzyloxycarbonyl)azetidin-3-yl)benzo[d]oxazole-7-carboxylate (280 mg, 0.76 mmol) was added to ammonia water (10 ml) and the mixture was stirred at 35° C. for overnight. Then the solid was filtered. 160 mg of benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)azetidine-1-carboxylate was obtained, yield 60%. LC-MS (ESI) m/z: 352 (M+1)+. (M+1)+,

Workup

  1. filtrationThen the solid was filtered

Sources & evidence

ORD record
ord-e6454250e1ee489089c1a04f08d020eb
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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