Diisopropylethylamine → HCID 57936037, compound

HRID 1912486Notes

Reaction equation

HRID 1912486 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH3:15])([CH3:14])[CH2:10][C:11]([OH:13])=O)=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.Cl.[CH2:53]([O:55][C:56](=[O:59])[CH2:57][NH2:58])[CH3:54]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([CH3:15])([CH3:14])[CH2:10][C:11]([NH:58][CH2:57][C:56]([O:55][CH2:53][CH3:54])=[O:59])=[O:13])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 57936042HCID 57936042, compound

Product 1

HCID 57936037HCID 57936037, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-chlorophenylamino)-3-methylbutanoic acid (1 g, 4.7 mmol) in CH2Cl2 (20 mL), was added BOP (2.07 g, 4.7 mmol), DIPEA (1.63 mL, 9.4 mmol) and glycine ethyl ester hydrochloride (0.79 g, 4.7 mmol). The mixture was stirred at rt overnight. The reaction was quenched with aq. NaHCO3, extracted with CH2Cl2, and the combined organic extracts were dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography using 0-30% EtOAc in hexanes as eluent to give ethyl 2-(3-(4-chlorophenylamino)-3-methylbutanamido)acetate (1.34 g, 96% yield) as a yellow oil.

Workup

  1. customThe reaction was quenched with aq. NaHCO3
  2. extractionextracted with CH2Cl2
  3. dry with materialthe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-597555365d14423dbd892ad9508087a5
Source dataset
uspto-grants-2013_12
Patent number
US08609664B2

Reaction notes

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