Benzyl chloroformate → HCID 54438009, compound

HRID 1003891Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>C(#N)C>[CH2:25]([O:24][C:22](=[O:23])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10](=[O:14])[CH:11]([CH3:12])[CH3:13])=[CH:6][CH:7]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 11.9 g (62 mmol) of crude 5-(4-amino-phenyl)-2-methyl-pentan-3-one (prepared in Example GGGGG) in 100 mL of acetonitrile was treated with 24.3 g (75 mmol) of cesium carbonate, and the mixture was stirred at 50° C. for 15 minutes. Benzyl chloroformate (10.7 mL, 75 mmol) was added all at once, and the mixture was stirred at room temperature for 90 minutes. The solvent was evaporated. The residue was partitioned between EtOAc and H2O; the organic layer was separated, washed with brine, dried (MgSO4), and concentrated. The product was chromatographed on silica gel, eluting with EtOAc:hexane (30:70), to give the title compound. 1H NMR (CDCl3) δ 1.01 (d, 6 H), 2.48-2.55 (m, 1 H), 2.67-2.82 (m,4 H), 5.15 (s, 2 H), 6.58 (br s, 1 H), 7.08 (d, 2 H), 7.25-7.38 (m, 7 H).

Workup

stirringwas stirred at room temperature for 90 minutes
customThe solvent was evaporated
customThe residue was partitioned between EtOAc and H2O
customthe organic layer was separated
washwashed with brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe product was chromatographed on silica gel
washeluting with EtOAc:hexane (30:70)

Sources & evidence

ORD record: ord-a940bd613ba34baaaf4157ffb8f2481c
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06046355

Reaction notes

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