Diisopropylethylamine → HCID 49835673, compound

HRID 1367459Notes

Reaction equation

HRID 1367459 reaction equation
[C:1]1([S:7]([C@@H:10]2[CH2:14][C@@H:13]([C:15]([OH:17])=O)[C@H:12]([C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:27][CH2:28][C:29]#[N:30].C(N(C(C)C)CC)(C)C.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[C:28]([CH2:29][NH:30][C:15]([C@@H:13]1[CH2:14][C@@H:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:8])=[O:9])[CH2:11][C@H:12]1[C:18]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:19])=[O:17])#[N:27]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11491918Aminoacetonitrile hydrochlorideHCID 66918645HCID 66918645, compound

Product 1

HCID 49835673HCID 49835673, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (1R,2R,4S)-4-benzenesulfonyl-2-(morpholine-4-carbonyl)-cyclopentanecarboxylic acid (0.1 mmol) and amino-acetonitrile hydrochloride (0.12 mmol) in dimethylformamide (0.5 ml) was subsequently treated with diisopropylethyl amine (0.5 mmol), 1-hydroxybenzotriazole hydrate (0.2 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 0.2 mmol) and stirring was continued at 22° C. overnight. The mixture was purified by preparative HPLC on a RP-18 column using a gradient of a mixture of acetonitrile and water to give (1R,2R,4R)-4-benzenesulfonyl-2-(morpholine-4-carbonyl)-cyclopentanecarboxylic acid cyanomethyl-amide as a white solid. MS: 406.5 (M+H)+.

Workup

  1. customThe mixture was purified by preparative HPLC on a RP-18 column
  2. additiona gradient of a mixture of acetonitrile and water

Sources & evidence

ORD record
ord-91525cf60f764d5dac8299a0a77f5ad7
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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