Dichloromethane → HCID 86591797, compound

HRID 2056645Notes

Reaction equation

HRID 2056645 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl[C:25](OCC1C2C=CC=CC=2C2C1=CC=CC=2)=[O:26].ClCCl>CC(C)=O.O>[C:25](=[C:14]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[CH:10]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([NH2:1])[CH:3]=1)[C:11]([OH:13])=[O:12])=[O:26]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 343679-Fluorenylmethyl chloroformateHCID 17855232HCID 17855232, compound

Product 1

HCID 86591797HCID 86591797, compoundYield 153.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Procedure

2-(3-amino-4-methoxyphenyl)-3-(4-nitrophenyl) propionic acid (6.20 g, 19.6 mmol) was dissolved in a mixed solvent of acetone (50 mL) and water (50 mL), and was gradually added with an acetone solution (50 mL) of 9-fluorenylmethyl chloroformate (5.08 g, 19.6 mmol) over 30 minutes in a drop-wise manner at 0° C. The mixture was heated to room temperature, and further stirred for 3 hours. The mixture was then added with dichloromethane (200 mL) and water (300 mL). The separated aqueous phase was extracted with dichloromethane (150 mL) three times. The extracts were mixed with the first organic phase, and washed twice with a saturated brine (150 mL). The organic phase was dried over sodium sulfate, evaporated under reduced pressure so as to remove the solvent, to thereby obtain N-fluoronylmethoxy carbonyl-2-(3-amino-4-methoxyphenyl)-3-(4-nitrophenyl) propionic acid (yield: 10.3 g, yield ratio: 97%).

Workup

  1. extractionThe separated aqueous phase was extracted with dichloromethane (150 mL) three times
  2. additionThe extracts were mixed with the first organic phase
  3. washwashed twice with a saturated brine (150 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customevaporated under reduced pressure so as
  6. customto remove the solvent

Sources & evidence

ORD record
ord-b3c383cdb38a42e285722e9c606158b7
Source dataset
uspto-grants-2008_02
Patent number
US07335673B2

Reaction notes

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