1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86614209, compound

HRID 888089Notes

Reaction equation

HRID 888089 reaction equation
[CH3:1][C:2]1([CH3:14])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][CH2:3]1.[O:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](O)=[O:21].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:1][C:2]1([CH3:14])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([C:20]([C@@H:16]2[CH2:17][CH2:18][CH2:19][O:15]2)=[O:21])[CH2:3]1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 446666Tetrahydro-2-furoic acid, (-)-HCID 219594663,3-Dimethyl-6-nitroindoline

Product 1

HCID 86614209HCID 86614209, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,3-dimethyl-6-nitroindoline (385 mg, 2 mmol), (S)-tetrahydrofuran-2-carboxylic acid (250 mg, 2.2 mmol), HOBt (266 mg, 2 mmol), EDAC (700 mg, 3.5 mmol), and DIEA (2 mL) in DCM (50 ml) was stirred at RT for overnight. The reaction mixture was washed in turn with aqueous NaHCO3 (sat., 50 mL), aqueous HCl (0.5N, 50 mL), H2O (50 mL), and brine (50 mL). The DCM layer was concentrated in vacuum to give the desired compound. MS: (ES+) 291(M+H). Calc'd. for C15H18N2O4—290.31.

Workup

  1. washThe reaction mixture was washed in turn with aqueous NaHCO3 (sat., 50 mL), aqueous HCl (0.5N, 50 mL), H2O (50 mL), and brine (50 mL)
  2. concentrationThe DCM layer was concentrated in vacuum

Sources & evidence

ORD record
ord-95d1d8789d064e658928fd332fb939c4
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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