Triethylamine → HCID 23589348, compound

HRID 1609823Notes

Reaction equation

HRID 1609823 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([NH:14][C:15](=[O:22])[CH:16]([OH:21])[CH2:17][CH:18]([CH3:20])[CH3:19])[C:11](=O)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:23]1([C:29](Cl)=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.CCN(CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][CH2:9][CH:10]([NH:14][C:15]([CH:16]([O:21][C:29]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:30])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:22])[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 23589511HCID 23589511, compound

Product 1

HCID 23589348HCID 23589348, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-hydroxy-4-methyl-pentanoic acid (2-benzyloxy-1-carbamoyl-ethyl)-amide (0.169 g, 0.55 mmol) in CH2Cl2 (5 mL) was added 4-morpholinecarbonyl chloride (0.082 g, 0.55 mmol), Et3N (0.15 mL, 1.1 mmol) and DMAP (0.034 g, 0.27 mmol). The resulting mixture was allowed to stir overnight (20 h) under argon at room temperature. When the reaction was complete the mixture was diluted with CH2Cl2 (10 mL), then washed with HCl (1.0 N, 10 mL), water and brine, dried over Na2SO4, and concentrated to give the desired product as an off-white oil in 0.20 g 86% yield of the crude product which was chromatographed (SiO2, 5% hexanes in EtOAc) to give desired product in (0.12 g, 52%). (e) Morpholine-4-carboxylic acid 1-[(benzyloxymethyl-cyano-methyl)-carbamoyl]-3-methyl-butyl Ester

Workup

  1. washwashed with HCl (1.0 N, 10 mL), water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-67ad49d665604d14b4c01a06be16fa7f
Source dataset
uspto-grants-2006_01
Patent number
US06982263B2

Reaction notes

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