m-Tolyl isocyanate → HCID 69248876, compound

HRID 1349205Notes

Reaction equation

C(O[C:6]([N:8]1[CH2:15][C:14](=[O:16])[CH2:13][C@H:9]1[C:10]([OH:12])=O)=[O:7])(C)(C)C.[N:17]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=1)=C=O.[NH:27]1[CH2:30][CH:29]([OH:31])[CH2:28]1>>[OH:31][CH:29]1[CH2:30][N:27]([C:10]([C@@H:9]2[CH2:13][C:14](=[O:16])[CH2:15][N:8]2[C:6]([NH:17][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=2)=[O:7])=[O:12])[CH2:28]1

Participants

Reactant 3

HCID 69303m-Tolyl isocyanate

HCID 15142903-Hydroxyazetidine

HCID 11593804(2S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid

Product 1

HCID 69248876HCID 69248876, compound

Procedure

Following the general method as outlined in Example 22, starting from 1-(tert-butoxycarbonyl)-4-oxoproline, 1-isocyanato-3-methylbenzene, and 3-azetidinol the title compound was obtained in 73% purity by LC/MS. MS(ESI+): m/z=318.0.

Sources & evidence

ORD record: ord-756cac0e47554cbca51c4095c721ab36
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211601B2

Reaction notes

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