N-Methylbenzylamine → (2S,4EZ)-1-[(benzoylamino)carbonyl]-N-benzyl-4-[(benzyloxy)imino]-N-methyl-2-pyrrolidinecarboxamide

HRID 1349042Notes

Reaction equation

HRID 1349042 reaction equation
[CH2:1]([O:8][N:9]=[C:10]1[CH2:14][N:13]([C:15]([O:17]C(C)(C)C)=O)[C@H:12]([C:22]([OH:24])=O)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([N:33]=C=O)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH2:36]([NH:43][CH3:44])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[C:25]([NH:33][C:15]([N:13]1[CH2:14][C:10](=[N:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:11][C@H:12]1[C:22]([N:43]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH3:44])=[O:24])=[O:17])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 7669N-MethylbenzylamineHCID 78210Benzoyl isocyanateHCID 131725420(2S,4EZ)-4[(benzyloxy)imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725426(2S,4EZ)-1-[(benzoylamino)carbonyl]-N-benzyl-4-[(benzyloxy)imino]-N-methyl-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-4-[(benzyloxy)imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, benzoyl isocyanate, and N-benzyl-N-methylamine the title compound was obtained in 40% purity by LC/MS. MS(ESI+): m/z=485.4.

Sources & evidence

ORD record
ord-d343d291c5084e9bad7d457224292fc3
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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