Tert-butyl 3-aminoazetidine-1-carboxylate → tert-butyl 3-[([{2S,4EZ)-4-(ethoxyimino)-1-[(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl]pyrrolidinyl}carbonyl)amino]-1-azetidinecarboxylate

HRID 1349047Notes

Reaction equation

HRID 1349047 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH2:15][CH3:16])[CH2:10][C@H:9]1[C:17]([OH:19])=O)=[O:7])(C)(C)C.[O:20]=[C:21]1[C:26](C(Cl)=O)=[CH:25][CH:24]=[C:23]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[O:22]1.[NH2:35][CH:36]1[CH2:39][N:38]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:37]1>>[CH2:15]([O:14][N:13]=[C:11]1[CH2:12][N:8]([C:6]([C:26]2[C:21](=[O:20])[O:22][C:23]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:24][CH:25]=2)=[O:7])[C@H:9]([C:17]([NH:35][CH:36]2[CH2:37][N:38]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:39]2)=[O:19])[CH2:10]1)[CH3:16]

Participants

4

Reactant 3

HCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 222235122-oxo-6-pentyl-2H-pyran-3-carbonyl chlorideHCID 58714540(2S,4EZ)-1-(tertbutoxycarbonyl)-4-(ethoxyirnino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131726368tert-butyl 3-[([{2S,4EZ)-4-(ethoxyimino)-1-[(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl]pyrrolidinyl}carbonyl)amino]-1-azetidinecarboxylate

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(ethoxyimino)-2-pyrrolidinecarboxylic acid, 2-oxo-6-pentyl-2H-pyran-3-carbonyl chloride, and tert-butyl 3-amino-1-azetidinecarboxylate the title compound was obtained in 100% purity by LC/MS. MS(ESI+): m/z=519.6.

Sources & evidence

ORD record
ord-20302e6526cb4faa90b26cb1d1fa0804
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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