Potassium Carbonate → (S)-methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-nitrophenyl)propanoate

HRID 2197389Notes

Reaction equation

HRID 2197389 reaction equation
[C:1](Cl)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].[NH2:19][C@@H:20]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)[C:21]([O:23][CH3:24])=[O:22].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[CH:16]1[C:17]2[CH:5]([CH2:4][O:3][C:1]([NH:19][C@@H:20]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)[C:21]([O:23][CH3:24])=[O:22])=[O:2])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 74082814-Nitro-L-phenylalanine methyl ester

Product 1

HCID 14284321(S)-methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-nitrophenyl)propanoateYield 100.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

Fmoc-Cl (27.6 g, 107.2 mmol) in 1,4-dioxane (950 mL) was added dropwise to a solution of (S)-methyl 2-amino-3-(4-nitrophenyl)propanoate (3A; 20 g, 89.3 mmol) and K2CO3 (14.8 g , 107.2 mmol) in water (80 mL) and 1,4-dioxane (150 mL) on an ice bath. After being stirred for 2 hours at room temperature, the mixture was poured into 1.2 L of water to precipitate a white solid, which was filtered and washed with cold water. The solid was dried under vacuum for 3 hours to give 40 g of (S)-methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-nitrophenyl)propanoate 3B, which was directly used in step 2.

Workup

  1. customto precipitate a white solid, which
  2. filtrationwas filtered
  3. washwashed with cold water
  4. customThe solid was dried under vacuum for 3 hours

Sources & evidence

ORD record
ord-770716348f7b426bbdcbf63b4308c540
Source dataset
uspto-grants-2012_12
Patent number
US08338565B2

Reaction notes

Loading…