2-Methoxyethylamine → (2S,4EZ)-4-(tert-butoxyimino)-N2-(2-methoxyethyl)-N1-(3-methoxyphenyl)-1,2-pyrrolidinedicarboxamide

HRID 1349172Notes

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.[N:22]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=1)=C=O.[CH3:33][O:34][CH2:35][CH2:36][NH2:37]>>[C:15]([O:14][N:13]=[C:11]1[CH2:12][N:8]([C:6]([NH:22][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=2)=[O:7])[C@H:9]([C:19]([NH:37][CH2:36][CH2:35][O:34][CH3:33])=[O:21])[CH2:10]1)([CH3:16])([CH3:17])[CH3:18]

Participants

Reactant 3

HCID 80182-Methoxyethylamine

HCID 878433-Methoxyphenyl isocyanate

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

Product 1

HCID 131725525(2S,4EZ)-4-(tert-butoxyimino)-N2-(2-methoxyethyl)-N1-(3-methoxyphenyl)-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-isocyanato-3-methoxybenzene, and 2-methoxyethylamine the title compound was obtained in 76% purity by LC/MS. MS(ESI+): m/z=407.2.

Sources & evidence

ORD record: ord-406598b3388447d59f1ffcdc6139465e
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211601B2

Reaction notes

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