Benzyl chloroformate → HCID 86752671, compound

HRID 1292376Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH2:20][CH2:21][NH2:22])=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25].C(N(C(C)C)CC)(C)C>>[CH2:27]([O:26][C:24](=[O:25])[NH:22][CH2:21][CH2:20][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Reactant 3

HCID 10387Benzyl chloroformate

HCID 81531Diisopropylethylamine

HCID 368016595426-76-9

Product 1

HCID 86752671HCID 86752671, compound

Conditions

Temperature: 0 °C

Procedure

To a suspension of 2-[2-(3,4-dimethoxyphenyl)-1H-indol-3-yl]ethylamine (150 mg in 1.5 mL methylene chloride) at -78° C. was added benzyl chloroformate (0.08 mL) and diisopropylethyl amine (0.093 mL) and the mixture warmed to 0° C. After 40 minutes, the reaction was quenched by the addition of saturated ammonium chloride, extracted with ethyl acetate and the organic portion dried over sodium sulfate. Purification by flash chromatography on silica gel (hexane:ethyl acetate, 2:1) gave the title compound (220 mg).

Workup

customthe reaction was quenched by the addition of saturated ammonium chloride
extractionextracted with ethyl acetate
dry with materialthe organic portion dried over sodium sulfate
customPurification by flash chromatography on silica gel (hexane:ethyl acetate, 2:1)

Sources & evidence

ORD record: ord-c0dfdf5647cf47aea579d76de85f0f8f
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05756507

Reaction notes

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