Benzyl chloroformate → HCID 54438009, compound

HRID 356536Notes

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-93a0181988f34f97abb8aad4aea17a7c
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05834506

Reaction notes

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