Tert-Butylamine → HCID 20309488, compound

HRID 972770Notes

Reaction equation

HRID 972770 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])=[C:4]([O:17][CH2:18][CH:19]2[O:21][CH2:20]2)[CH:3]=1.[C:22]([NH2:26])([CH3:25])([CH3:24])[CH3:23]>>[C:22]([NH:26][CH2:20][CH:19]([OH:21])[CH2:18][O:17][C:4]1[CH:3]=[C:2]([Cl:1])[CH:16]=[CH:15][C:5]=1[C:6]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:25])([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 20309476HCID 20309476, compound

Product 1

HCID 20309488HCID 20309488, compoundYield 88%

Procedure

A stirred mixture of ethyl 3-[4-chloro-2-(2,3-epoxypropoxy)benzoyl]propionate (3.0 g, 0.01 mole) methanol (28 ml) and t-butylamine (6.7 ml, 0.0625 mole) was heated under reflux for 70 minutes. The mixture was evaporated to an oily residue which was purified on a silica column by elution with mixtures of chloroform and methanol and recrystallisation from ether-petroleum ether (b.p. 40°-60°) to give ethyl 3-[2-(3-t-butylamino-2-hydroxypropoxy)-4-chlorobenzoyl]propionate (3.18 g, 88%, m.p. 70°).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 70 minutes
  3. customThe mixture was evaporated to an oily residue which
  4. customwas purified on a silica column by elution with mixtures of chloroform and methanol and recrystallisation from ether-petroleum ether (b.p. 40°-60°)

Sources & evidence

ORD record
ord-636a420c1b664dcbbc46e875a1d102fa
Source dataset
uspto-grants-1977_10
Patent number
US04053601

Reaction notes

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