N-(2-Acetyl-phenyl)-2,3-dihydroxy-3-methyl-butyramide → N-[2-(1-Allylamino-ethyl)-phenyl]-2,3-dihydroxy-3-methyl-butyramide

HRID 584778Notes

Reaction equation

HRID 584778 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:18])[CH:12]([OH:17])[C:13]([OH:16])([CH3:15])[CH3:14])(=O)[CH3:2]>C(OCC)(=O)C.CCCCCC>[CH2:5]([NH:10][CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:18])[CH:12]([OH:17])[C:13]([OH:16])([CH3:15])[CH3:14])[CH3:2])[CH:4]=[CH2:1]

Participants

3

Reactant 1

HCID 22341823N-(2-Acetyl-phenyl)-2,3-dihydroxy-3-methyl-butyramide

Product 1

HCID 22341801N-[2-(1-Allylamino-ethyl)-phenyl]-2,3-dihydroxy-3-methyl-butyramide

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Prepared analogously to Example 11, starting with the product of Example 13 in 29% isolated yield (mixture of diastereomers), from flash column chromatography in ethyl acetate-hexane (3:2 to 4:1). 1H NMR (250 MHz, CDCl3) δ 8.35-8.18 (m, 1H), 7.30-7.19 (m, 1H), 7.15-6.98 (m, 2H), 5.99-5.77 (m, 1H), 5.23-5.03 (m, 2H), 4.06-3.91 (m, 2H), 3.13 (d, J=5.6 Hz, 2H), 1.42 (d, J=6.7 Hz, 3H), 1.31 (s, 3H), 1.29 (d, J=2.5 Hz, 3H).

Workup

  1. customPrepared analogously to Example 11
  2. customisolated
  3. customyield
  4. addition(mixture of diastereomers)

Sources & evidence

ORD record
ord-0fe4d4d4ffaa4fe1a238894deba45561
Source dataset
uspto-grants-2005_08
Patent number
US06927294B1

Reaction notes

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