3,5-Xylyl isocyanate → HCID 70558281, compound

HRID 408615Notes

Reaction equation

Cl.[CH3:2][O:3][C:4](=[O:24])[CH2:5][CH2:6][CH2:7][N:8]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:9]([C:11]1([CH3:15])[CH2:14][CH2:13][NH:12]1)=[O:10].[CH3:25][C:26]1[CH:27]=[C:28]([N:33]=[C:34]=[O:35])[CH:29]=[C:30]([CH3:32])[CH:31]=1>C1COCC1>[CH3:2][O:3][C:4](=[O:24])[CH2:5][CH2:6][CH2:7][N:8]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=1)[C:9]([C:11]1([CH3:15])[CH2:14][CH2:13][N:12]1[C:34](=[O:35])[NH:33][C:28]1[CH:29]=[C:30]([CH3:32])[CH:31]=[C:26]([CH3:25])[CH:27]=1)=[O:10]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 4-[(4-chloro-benzyl)-(2-methyl-azetidine-2-carbonyl)-amino]-butyric acid methyl ester hydrochloride, Intermediate 23 (1 eq.) and TEA (5 eq.) in THF under nitrogen was added 3,5-dimethyl-phenyl-isocyanate (1.5 eq.). The reaction was stirred for 15 h at 20° C. The crude was partitioned between a saturated aqueous solution of NaHCO3 and EtOAc. The organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 75/25 to 40/60) to afford 4-{(4-chloro-benzyl)-[1-(3,5-dimethyl-phenylcarbamoyl)-2-methyl-azetidine-2-carbonyl]-amino}-butyric acid methyl ester.

Workup

customThe crude was partitioned between a saturated aqueous solution of NaHCO3 and EtOAc
washThe organic layer was washed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 75/25 to 40/60)

Sources & evidence

ORD record: ord-d2bb5d29b6034cd5905b00c286bd6f73
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759334B2

Reaction notes

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