Aminoacetonitrile → HCID 86649022, compound

HRID 1367492Notes

Reaction equation

HRID 1367492 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH:11]1[CH2:15][C@@H:14]([C:16]([OH:18])=O)[C@H:13]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH2:12]1)(=[O:10])=[O:9].Cl.CN(C)CCCN=C=NCC.OC1[C:49]2[N:48]=N[NH:46][C:45]=2C=CC=1.C(N(C(C)C)C(C)C)C.NCC#N>CN(C)C=O>[C:45]([CH2:49][NH:48][C:16]([C@@H:14]1[CH2:15][CH:11]([S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])(=[O:10])=[O:9])[CH2:12][C@H:13]1[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)=[O:18])#[N:46]

Participants

7

Reactant 5

HCID 10901AminoacetonitrileHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66919040HCID 66919040, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 86649022HCID 86649022, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (1R,2R)-4-(2-Chloro-benzenesulfonyl)-2-(4-chloro-phenoxymethyl)-cyclopentanecarboxylic acid (epimeric mixture, 50 mg) in dimethylformamide (2 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (46 mg), hydroxybenzotriazole (24 mg) and ethyldiisopropylamine (61 mg). After 45 min, aminoacetonitrile (8 mg) was added and the reaction mixture was stirred for 2 days then partitioned between ethyl acetate and an aqueous saturated solution of sodium hydrogenocarbonate. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water then dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with dichloromethane/methanol (19:1 v/v) as eluant to afford the title compound (53 mg, 97%) as light yellow oil. MS (EI): 467.0 (M+H)+.

Workup

  1. customthen partitioned between ethyl acetate
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layers were washed with water
  4. dry with materialthen dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel with dichloromethane/methanol (19:1 v/v) as eluant

Sources & evidence

ORD record
ord-6684a4eac30d4ed784a4d836738c4a16
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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