Cesium carbonate → methyl N-(t-butyloxycarbonyl)-2-amino-2-[4-(2,6-dimethoxyphenyl)phenyl]acetate

HRID 2236143Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17](OS(C2C(C)=CC=CC=2)(=O)=O)=[CH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[CH3:56][O:57][C:58]1[CH:63]=[CH:62][CH:61]=[C:60]([O:64][CH3:65])[C:59]=1B(O)O>O1CCOCC1.C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni]>[C:1]([O:5][C:6]([NH:8][CH:9]([C:14]1[CH:15]=[CH:16][C:17]([C:59]2[C:58]([O:57][CH3:56])=[CH:63][CH:62]=[CH:61][C:60]=2[O:64][CH3:65])=[CH:18][CH:19]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 70 °C

Procedure

Under a nitrogen atmosphere, methyl N-(t-butyloxycarbonyl)-2-amino-2-(4-toluenesulfonyloxyphenyl)acetate (0.44 g, 1.0 mmol), cesium carbonate (0.65 g, 2.0 mmol), tricyclohexylphosphine (0.059 g, 0.2 mmol), bis(1,5-cyclooctadiene)nickel (0.028 g, 0.1 mmol) and 2,6-dimethoxyphenylboronic acid (0.36 g, 2.0 mmol) were mixed in dioxane (1 ml). The reaction mixture was heated to 70° C. and then stirred at the same temperature for 9 hrs. After the reaction was completed, the mixture was left to cool to room temperature and insoluble substances were filtered off. The filtrate was subjected to column chromatography purification to obtain methyl N-(t-butyloxycarbonyl)-2-amino-2-[4-(2,6-dimethoxyphenyl)phenyl]acetate (0.29 g, yield 72%) as pale yellow oil.

Workup

waitthe mixture was left
temperatureto cool to room temperature
filtrationinsoluble substances were filtered off
customThe filtrate was subjected to column chromatography purification

Sources & evidence

ORD record: ord-79e0bf1c298c46b89706f37e57838ada
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714157B2

Reaction notes

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