Ethylmorpholine → HCID 58031792, compound

HRID 240257Notes

Reaction equation

HRID 240257 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[C:10]([O-])(=O)[CH2:11][C:12]([O-])=O.[CH2:17](N1CCOCC1)C.[CH:25]1[CH:30]=[C:29]2N=N[N:33](O)[C:28]2=[CH:27][CH:26]=1.O.CCN=C=NCCCN(C)C.[C:47]([C:51]1[CH:52]=[C:53]([CH:60]=[CH:61][CH:62]=1)[O:54][CH:55]([CH3:59])[C:56]([OH:58])=O)([CH3:50])([CH3:49])[CH3:48]>CN(C=O)C>[C:47]([C:51]1[CH:52]=[C:53]([CH:60]=[CH:61][CH:62]=1)[O:54][CH:55]([CH3:59])[C:56]([NH:33][C:28]1[CH:27]=[CH:26][C:25]([CH:10]([CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])[C:11]#[C:12][CH3:17])=[CH:30][CH:29]=1)=[O:58])([CH3:48])([CH3:49])[CH3:50]

Participants

8

Reactant 6

HCID 7525EthylmorpholineHCID 7943Dimethyl malonateHCID 9084Malonate IonHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 167701622-(3-TERT-BUTYLPHENOXY)PROPANOIC ACID

Product 1

HCID 58031792HCID 58031792, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 250 mg (0.91 mmol) of dimethyl malonate, malonate, 314 mg (2.72 mmol) of N-ethylmorpholine, 153 mg (1.0 mmol) of HOBt hydrate and 155 mg (1.0 mmol) of EDAC in 7 ml of DMF was added a solution of 202 mg (0.91 mmol) of 2-(3-tert-butylphenoxy)propionic acid in 3 ml of DMF. After 18 h at room temperature, the reaction mixture was concentrated completely and separated by means of preparative HPLC (Merck Hibar Purospher Star RP-18e 10 μm 25×250 mm; A: H2O+0.05% TFA; B: ACN+0.05% TFA; flow rate: 50 ml/min; in 15 minutes 10% B→90% B). The product fractions were freeze-dried to give 323 mg (74%) of dimethyl 2-(1-{4-[2-(3-tert-butylphenoxy)propionylamino]phenyl}but-2-ynyl)malonate.

Workup

  1. concentrationthe reaction mixture was concentrated completely
  2. customseparated by means of preparative HPLC (Merck Hibar Purospher Star RP-18e 10 μm 25×250 mm
  3. waitin 15 minutes 10% B→90% B)
  4. customThe product fractions were freeze-dried

Sources & evidence

ORD record
ord-e2a33a9e7c614756bacfb986dfeaf445
Source dataset
uspto-grants-2014_02
Patent number
US08648038B2

Reaction notes

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