Diisopropylethylamine → HCID 69641469, compound

HRID 1828114Notes

Reaction equation

HRID 1828114 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH:5]([O:9][CH2:10][CH3:11])[C:6]([OH:8])=O)[CH3:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[NH2:41][CH2:42][C:43]1[CH:50]=[CH:49][C:46]([C:47]#[N:48])=[CH:45][CH:44]=1.C(N(C(C)C)C(C)C)C>C1COCC1>[CH2:1]([O:3][C:4](=[O:12])[CH:5]([O:9][CH2:10][CH3:11])[C:6]([NH:48][CH2:47][C:46]1[CH:49]=[CH:50][C:43]([C:42]#[N:41])=[CH:44][CH:45]=1)=[O:8])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 99422504-(Aminomethyl)benzonitrile hydrochlorideHCID 544224782-Ethoxy-malonic acid monoethyl ester

Product 1

HCID 69641469HCID 69641469, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution under N2 of (RS)-2-ethoxy-malonic acid monoethyl ester (666 mg, 1.0) in THF (37 ml) was prepared. BOP (2.17 g), 4-aminomethyl-benzonitrile hydrochloride (555 mg) and N-ethyldiisopropylamine (733 mg) were added at 0° C. The ice bath was removed and the reaction was let to stir 24 h. THF was evaporated and the mixture was diluted with EtOAc. This organic phase was washed with a sat. aq. NaHCO3 sol. and with brine. The aqueous phases were extracted with one more portion of EtOAc and dried over MgSO4. The solvent was evaporated. The crude product was purified by flash chromatography. (heptane/EtOAc 3:1 to 2:1). 750 mg (68%) of (RS)-N-(4-cyano-benzyl)-2-ethoxy-malonamic acid ethyl ester were isolated as a yellow oil. MS 308.4 (100, [M+NH4]+), 291.1 (88, [M+H]+).

Workup

  1. customThe ice bath was removed
  2. customTHF was evaporated
  3. additionthe mixture was diluted with EtOAc
  4. washThis organic phase was washed with a sat. aq. NaHCO3 sol. and with brine
  5. extractionThe aqueous phases were extracted with one more portion of EtOAc
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated
  8. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-5f998aaa7dbf4c5c94eb3e11fd598f47
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

Loading…