Cyclopropylamine → (2S,4EZ)-4-(tert-butoxyimino)-N2-cyclopropyl-N1-(3,5-dichlorophenyl)-1,2-pyrrolidinedicarboxamide

HRID 1349040Notes

Reaction equation

C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][C@H:9]1[C:19]([OH:21])=O)=[O:7])(C)(C)C.[Cl:22][C:23]1[CH:28]=[C:27]([N:29]=C=O)[CH:26]=[C:25]([Cl:32])[CH:24]=1.[CH:33]1([NH2:36])[CH2:35][CH2:34]1>>[C:15]([O:14][N:13]=[C:11]1[CH2:12][N:8]([C:6]([NH:29][C:27]2[CH:28]=[C:23]([Cl:22])[CH:24]=[C:25]([Cl:32])[CH:26]=2)=[O:7])[C@H:9]([C:19]([NH:36][CH:33]2[CH2:35][CH2:34]2)=[O:21])[CH2:10]1)([CH3:16])([CH3:17])[CH3:18]

Participants

Reactant 3

HCID 69828Cyclopropylamine

HCID 944603,5-Dichlorophenyl isocyanate

HCID 131725425(2S,4EZ)-1-(tertbutoxycarbonyl)-4-(tert-butoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725424(2S,4EZ)-4-(tert-butoxyimino)-N2-cyclopropyl-N1-(3,5-dichlorophenyl)-1,2-pyrrolidinedicarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(tert-butoxyimino)-2-pyrrolidinecarboxylic acid, 1,3-dichloro-5-isocyanatobenzene, and cyclopropylamine the title compound was obtained in 48% purity by LC/MS. MS(ESI+): m/z=427.6.

Sources & evidence

ORD record: ord-46f4fa17c6074fcb8164acbe8a27d52f
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211601B2

Reaction notes

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