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

HRID 1389094
Notes
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Reaction equation

HRID 1389094 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344
Dichloromethane
Solvent

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-8aa8c122dc194730906bebafe7255833
Source dataset
uspto-grants-1981_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04243609

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes