tert-butyl N-(azetidin-3-ylmethyl)carbamate → benzyl N-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]azetidine-1-carboximidoyl]carbamate

HRID 871Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:13][NH:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:21][C:22]([NH:24][C:25](=[NH:28])OC)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:11][N:12]([C:25](=[NH:28])[NH:24][C:22]([O:21][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:23])[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

0.9 g (4.8 mmol) of 3-(N-tert-butyloxycarbonylaminomethyl) azetidine and 1.3 g (6.3 mmol) of N-benzyloxycarbonyl-O-methylisourea was mixed in 6.5 mL toluene and heated to 70° C. for 72 h and then left at room temperature for another 72 h. Evaporation followed by flash chromatography using EtOAc followed by MeOH (saturated with NH3 (g))/CH2 Cl2, 1/9, as eluent gave 0.67 g (38%) of the title compound as a white powder.

Workup

customEvaporation

Sources & evidence

ORD record: ord-6d13e77736d347fc8d7ecd3394515558
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723444

Reaction notes

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