2-Methoxyethylamine → HCID 18617759, compound

HRID 1264215Notes

Reaction equation

HRID 1264215 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=O)=[CH:8][CH:7]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH3:49][O:50][CH2:51][CH2:52][NH2:53]>C(Cl)Cl>[CH3:49][O:50][CH2:51][CH2:52][NH:53][C:13](=[O:15])[C:12]([C:9]1[CH:8]=[CH:7][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:11][CH:10]=1)([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 80182-MethoxyethylamineHCID 81531Diisopropylethylamine2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 18182605HCID 18182605, compound

Product 1

HCID 18617759HCID 18617759, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-(furan-2-yl)-phenyl)-2-methyl-propionic Acid (reference example 28) (344 mg, 1.5 mmol) in CH2Cl2 (4 mL) is added TBTU (528 mg, 1.65 mmol) followed by diisopropylethylamine (280 mL, 1.6 mmol). The resulting mixture is stirred for 2 h then a further portion of DIEA added (280 mL) along with 2-methoxy-ethylamine (225 mL, 2.6 mmol). The resulting solution is stirred for 90 minutes then concentrated. The residue is purified by flash chromatography (eluting with 10% CH2Cl2/50% ethyl acetate in hexanes) to give 380 mg of product as a white solid. 1H NMR (CD3OD) d 1.58 (s, 6H), 3.24 (s, 3H), 3.36 (m, 4H), 5.58 (bs, 1H), 6.47 (dd, J=3, 2 Hz, 1H), 6.65 (d, J=3 Hz, 1H), 7.41 (m, 2H), 7.49 (d, J=2 Hz, 1H), 7.65 (m, 2H). MS (EI) m/z 287 (M+).

Workup

  1. stirringThe resulting solution is stirred for 90 minutes
  2. concentrationthen concentrated
  3. customThe residue is purified by flash chromatography (eluting with 10% CH2Cl2/50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d8fc21574c344976bda438a38ad156ba
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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