Ammonium Acetate → HCID 58746911, compound

HRID 724741Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[I:30])[CH2:5][C@H:6]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:7](=O)[NH:8][CH2:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])(=O)C.[NH4+:35]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][C@H:6]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:7]2[NH:35][C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][N:8]=2)[CH:27]=[CH:28][C:29]=1[I:30]

Participants

Conditions

Temperature: 120 °C

Procedure

tert-Butyl (1S)-1-(3-chloro-4-iodobenzyl)-2-oxo-2-[(2-oxo-2-phenylethyl)-amino]ethylcarbamate (3.1 g, 5.7 mmol) and ammonium acetate (30.0 g, 0.389 mol) were dissolved in DMF (50 mL). The solution was separated into 6 batches, and each batch was heated in the microwave at 120° C. for 30 minutes. The solution was diluted with ethyl acetate (600 mL) and washed with water (600 mL). After the organic layer was dried over sodium sulfate, the solution was concentrated. Purification by silica gel chromatography (20–40% ethyl acetate:hexanes) afforded product as a white solid (2.0 g, 67%). 1H NMR (400 MHz, CD3OD): δ 7.86–7.78 (m, 2H), 7.73–7.68 (m, 2H), 7.59–7.50 (m, 3H), 7.40–7.37 (m, 1H), 6.89–6.87 (m, 1H), 5.13–5.11 (m, 1H), 3.40–3.25 (m, 2H), 1.38 (s, 9H). LCMS found for C22H24ClIN3O2 (M+H)+: m/z=524.

Workup

customThe solution was separated into 6 batches
additionThe solution was diluted with ethyl acetate (600 mL)
washwashed with water (600 mL)
dry with materialAfter the organic layer was dried over sodium sulfate
concentrationthe solution was concentrated
customPurification by silica gel chromatography (20–40% ethyl acetate:hexanes)

Sources & evidence

ORD record: ord-63917e69671f49e69d2cd673a7cb770d
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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