Diethyl Ether → 1-(Methoxycarbonyl)propyl 3-fluoro-4-(hexadecylamino)benzoate

HRID 1156118Notes

Reaction equation

HRID 1156118 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:6](Cl)=[O:7].[OH:29][CH:30]([CH2:35][CH3:36])[C:31]([O:33][CH3:34])=[O:32].C(N(CC)CC)C.CCOCC>C(Cl)Cl>[F:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:6]([O:29][CH:30]([C:31]([O:33][CH3:34])=[O:32])[CH2:35][CH3:36])=[O:7]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 520445Methyl 2-hydroxybutanoateHCID 205364403-Fluoro-4-hexadecylaminobenzoyl chloride hydrochloride

Product 1

HCID 205364811-(Methoxycarbonyl)propyl 3-fluoro-4-(hexadecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10.0 g 3-fluoro-4-(hexadecylamino)benzoyl chloride hydrochloride in 200 ml methylene chloride is added dropwise a solution of 3 g. methyl α-hydroxybutyrate and 5 g triethylamine in 100 ml. ether. After 17 hours stirring at room temperature, the precipitate is collected and washed with several portions of ether. The ether solution is washed with water, dried and evaporated to yield 1-(methoxycarbonyl)propyl 3-fluoro-4-(hexadecylamino)benzoate as a white solid.

Workup

  1. customthe precipitate is collected
  2. washwashed with several portions of ether
  3. washThe ether solution is washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-4f6c238cf62b4ae4b474f4862afe2b62
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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