Water → 1-(3-Acetoxy-4-methoxy-benzoylamino)-Cycloheptanecarboxylic Acid Methyl Ester

HRID 1918281Notes

Reaction equation

HRID 1918281 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8]([OH:10])=O)(=[O:3])[CH3:2].Cl.[CH3:17][O:18][C:19]([C:21]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:20].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.O>CN(C=O)C>[CH3:17][O:18][C:19]([C:21]1([NH:28][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 151620Benzoic acid, 3-(acetyloxy)-4-methoxy-HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 42614177Methyl 1-aminocycloheptane-1-carboxylate hydrochloride

Product 1

HCID 866725641-(3-Acetoxy-4-methoxy-benzoylamino)-Cycloheptanecarboxylic Acid Methyl EsterYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Acetoxy-4-methoxy-benzoic acid (7.10 g, 33.8 mmol) was dissolved in DMF (70 ml). The solution was cooled in an ice bath and 1-amino-cycloheptanecarboxylic acid methyl ester hydrochloride (7.72 g, 37.2 mmol), EDIA (24.4 ml, 135 mmol) and TOTU (16.6 g, 50.7 mmol) were added sequentially. Stirring was continued at room temperature for 1 h. Water was added and stirring was continued for 1 h. The solid material which formed was collected by filtration, washed with water and dried in vacuo. The obtained material was stirred with a diethyl ether/HEP mixture, filtered and dried in vacuo to yield the title compound (9.03 g).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. stirringstirring
  3. waitwas continued for 1 h
  4. customThe solid material which formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried in vacuo
  8. stirringThe obtained material was stirred with a diethyl ether/HEP mixture
  9. filtrationfiltered
  10. customdried in vacuo

Sources & evidence

ORD record
ord-4a5cd9db891847f89095fce0c9b326c9
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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