Diisopropylethylamine → 6-(Tert-butoxycarbonyl)-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylic acid

HRID 1183810Notes

Reaction equation

C1C2=C3C(=CC=C2NC1)NC(C(OC)=O)=C3.[C:17]([O:21][C:22]([N:24]1[C:35]2[C:27](=[C:28]3[C:32](=[CH:33][CH:34]=2)[NH:31][C:30]([C:36]([O:38]C)=[O:37])=[CH:29]3)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].CCN(C(C)C)C(C)C>CN(C=O)C>[C:17]([O:21][C:22]([N:24]1[C:35]2[C:27](=[C:28]3[C:32](=[CH:33][CH:34]=2)[NH:31][C:30]([C:36]([OH:38])=[O:37])=[CH:29]3)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4 (16 mg, 0.015 mmol) and 5 (6.2 mg, 0.02 mmol) in DMF (2 mL) was treated with DIPEA (10 uL). The reaction mixture was stirred for 1 hr at 25° C. The final product was purified by Prep HPLC (SymmetrPrep C18, 7 μm, 19×150 mm column), eluted at 10 ml/min (0.01% TFA in water/acetonitrile) with a gradient: 10% acetonitrile in 5 min, 10% to 50% acetonitrile in 15 min, maintaining 50% acetonitrile in 5 min, 50% to 100% acetonitrile in 5 min, to obtain 6 (13 mg, 75%). MS: calcd for C51H55BrN10O9 (M+H) m/z 1031.33 found 1031.6.

Workup

customThe final product was purified by Prep HPLC (SymmetrPrep C18, 7 μm, 19×150 mm column)
washeluted at 10 ml/min (0.01% TFA in water/acetonitrile) with a gradient
wait10% acetonitrile in 5 min
wait10% to 50% acetonitrile in 15 min
temperaturemaintaining 50% acetonitrile in 5 min
wait50% to 100% acetonitrile in 5 min

Sources & evidence

ORD record: ord-87bc94260e35482589960e4f3b6f30da
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664407B2

Reaction notes

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