Acetic Acid → HCID 59643291, compound

HRID 2251473Notes

Reaction equation

HRID 2251473 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1.[CH:18]([C:21]1[O:25][N:24]=[C:23]([C:26]2[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=2)[N:22]=1)([CH3:20])[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[CH:18]([C:21]1[O:25][N:24]=[C:23]([C:26]2[CH:27]=[CH:28][C:29]([CH2:30][NH:1][CH2:2][CH2:3][C:4]3[CH:5]=[CH:6][C:7]([O:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:16][CH:17]=3)=[CH:32][CH:33]=2)[N:22]=1)([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 21320401Methyl 2-[4-(2-aminoethyl)phenoxy]-2-methylpropanoateHCID 59643227HCID 59643227, compound

Product 1

HCID 59643291HCID 59643291, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-[4-(2-aminoethyl)phenoxy]-2-methylpropanoate (1 g; 4.22 mmol) in dichloromethane (30 ml) was treated under nitrogen with 4-(5-isopropyl-1,2,4-oxadiazol-3-yl)benzaldehyde (0.96 g; 4.43 mmol), sodium triacetoxyborohydride (0.94 g; 4.43 mmol) and acetic acid (0.24 ml; 4.23 mmol). After stirring at rt overnight, the mixture was concentrated and partitioned between ethyl acetate and 1N NaOH. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography using an ethyl acetate-hexane gradient (20–70%) followed by a methanol-dichloromethane gradient (1–10%) afforded the title compound (1.5 g; 81% yield).

Workup

  1. concentrationthe mixture was concentrated
  2. custompartitioned between ethyl acetate and 1N NaOH
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-07e31dd665af4f2591b7f0a0893f73df
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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