Tetrahydrofuran → HCID 23661730, compound

HRID 1364196Notes

Reaction equation

HRID 1364196 reaction equation
Cl.CN(C)[CH2:4][CH2:5][CH2:6][N:7]=C=NCC.O[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2N=N1.[CH:23](N(C(C)C)CC)([CH3:25])[CH3:24].[C:32]([O:36][C:37]([NH:39][C@H:40]([CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[O:51][C:52]([F:55])([F:54])[F:53])[C:41]([OH:43])=O)=[O:38])([CH3:35])([CH3:34])[CH3:33].[O:56]1CCC[CH2:57]1>O>[C:32]([O:36][C:37](=[O:38])[NH:39][C@@H:40]([C:41](=[O:43])[NH:7][C@@H:6]1[CH2:5][CH2:4][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:14]([CH:23]([CH3:25])[CH3:24])[C:57]1=[O:56])[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[O:51][C:52]([F:55])([F:54])[F:53])([CH3:34])([CH3:35])[CH3:33]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57779803HCID 57779803, compound

Product 1

HCID 23661730HCID 23661730, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the crude product described above (1.01 g), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.843 g, 4.39 mmol), 1-hydroxybenzotriazole (0.593 g, 4.39 mmol), diisopropylethylamine (1.90 mL, 11.0 mmol), the product from Step 3 (0.843 g, 2.42 mmol) and tetrahydrofuran (15 mL) was stirred for 18 hours at room temperature. The reaction was then diluted with H2O and extracted with ethyl acetate. The organic extracts were concentrated in vacuo and purified via flash chromatography on silica gel (0% to 50% ethyl acetate/hexanes linear gradient) to give the desired product.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic extracts were concentrated in vacuo
  3. custompurified via flash chromatography on silica gel (0% to 50% ethyl acetate/hexanes linear gradient)

Sources & evidence

ORD record
ord-3773f60c3e95436fbae38d49aa48957e
Source dataset
uspto-grants-2011_02
Patent number
US07888345B2

Reaction notes

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