Potassium Carbonate → HCID 90456922, compound

HRID 625884Notes

Reaction equation

HRID 625884 reaction equation
OC(C(F)(F)F)=O.[NH2:8][C@@H:9]([CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=1)[C:10]([OH:12])=[O:11].O1CCOCC1.C([O-])([O-])=O.[K+].[K+].[C:34](Cl)(=[O:50])[O:35][CH2:36][CH:37]1[C:49]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2>O>[CH:48]1[C:49]2[CH:37]([CH2:36][O:35][C:34]([NH:8][C@@H:9]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=3)[C:10]([OH:12])=[O:11])=[O:50])[C:38]3[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:44]=2[CH:45]=[CH:46][CH:47]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 343679-Fluorenylmethyl chloroformateHCID 131735210HCID 131735210, compound

Product 1

HCID 90456922HCID 90456922, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a round-bottom flask equipped with a stir bar and charged with the entirety of (S)-2-amino-3-(m-tolyloxy)propanoic acid TFA salt afforded in Step 3 (assumed 3.36 mmol) was added 1,4-Dioxane (4 mL) and water (16 mL), then K2CO3 (1.17 g, 8.49 mmol). The mixture was cooled to 0° C., then to the mixture was added (9H-fluoren-9-yl)methyl carbonochloridate (549 mg, 2.12 mmol). The mixture was allowed to warm to room temperature with stirring for 18 h. The mixture was diluted with water (10 mL) and then washed with diethyl ether (2×15 mL). The aqueous phase was acidified with aq. HCl (1M) to pH 2-3, and then was extracted with CH2Cl2 (3×20 ml). The combined CH2Cl2 solutions were dried over MgSO4; filtered; then concentrated in vacuo to afford (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(m-tolyloxy)propanoic acid as a white solid, 430 mg (31% over two steps).

Workup

  1. customTo a round-bottom flask equipped with a stir bar
  2. temperatureto warm to room temperature
  3. washwashed with diethyl ether (2×15 mL)
  4. extractionwas extracted with CH2Cl2 (3×20 ml)
  5. dry with materialThe combined CH2Cl2 solutions were dried over MgSO4
  6. filtrationfiltered
  7. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-d6f79976dbcb4a33bd3f31d6c4bb29cd
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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