Triethylamine → HCID 70242261, compound

HRID 1385911Notes

Reaction equation

HRID 1385911 reaction equation
[CH3:1][N:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=2)[CH2:5][C@H:4]([CH2:15][C:16]([OH:18])=O)[O:3]1.Cl.[CH3:20][O:21][C:22](=[O:26])[CH2:23][CH2:24][NH2:25].C(N(CC)CC)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[CH3:20][O:21][C:22](=[O:26])[CH2:23][CH2:24][NH:25][C:16](=[O:18])[CH2:15][C@@H:4]1[O:3][N:2]([CH3:1])[C@H:6]([C:7]2[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[CH:11][CH:12]=2)[CH2:5]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 20671782HCID 20671782, compound

Product 1

HCID 70242261HCID 70242261, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-[2-methyl-3(S)-(4-cyanophenyl)-isoxazolidin-5(R)-yl]acetic acid (500 mg, 2.0 mmol), b-alanine methyl ester HCl salt (314 mg, 2.4 mmol) and triethylamine (1.7 ml, 12 mmol) in DMF (7 ml), cooled with ice-water, was added PyBOP (1,18 g, 2.0 mmol). After stirring for 12 hrs, the reaction mixture was diluted with ethyl acetate and washed with dilute NaHCO3 and brine, then dried. Concentration followed by chromatography with a mixture of EtOAc and hexane as the eluent gave the product as an amorphous solid (660 mg, 98% yield).1H NMR (300 MHz, CDCl3) δ2.00 (m, 1H), 2.40(dd, 1H), 2.56(t, 2H), 2.60(s, 3H), 2.68(dd, 1H), 2.94(m, 1H), 3.54(qt, 2H), 3.68(t, 1H), 3.70(s, 3H), 4.60(m, 1H), 6.60(s, 1H), 7.46(d, 2H), 7.64(d, 2H); MS (ESI) Calc. for (M+1)+: 332. Found: 332.

Workup

  1. washwashed with dilute NaHCO3 and brine
  2. customdried
  3. concentrationConcentration
  4. additionfollowed by chromatography with a mixture of EtOAc and hexane as the eluent

Sources & evidence

ORD record
ord-908138a407ea4880a5adb47691cd1f0a
Source dataset
uspto-grants-2001_07
Patent number
US06265400B1

Reaction notes

Loading…