Dichloromethane → sarcosine-O-fluorenylmethyl ester hydrochloride salt

HRID 377459

Reaction equation

HRID 377459 reaction equation
C([N:8]([CH2:10][C:11]([OH:13])=[O:12])[CH3:9])(OC(C)(C)C)=O.[C:14]([C:21]1NC=CN=1)([C:16]1NC=CN=1)=O.[CH:26]1[C:38]2[CH:37](CO)C3[C:31](=[CH:32][CH:33]=[CH:34]C=3)[C:30]=2[CH:29]=[CH:28][CH:27]=1.[Cl:41]CCl>C(OCC)(=O)C>[ClH:41].[C:14]1([CH2:16][O:13][C:11](=[O:12])[CH2:10][NH:8][CH3:9])[C:21]2[CH2:37][C:38]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:31]=2[CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 904669H-Fluorene-9-methanolHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 131720354sarcosine-O-fluorenylmethyl ester hydrochloride saltYield 73%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Boc-sarcosine (30 g, 158 mmole) in 500 mL dichloromethane was added with stirring carbonyl diimidazole (25.7 g, 158 mmole). After 15 minutes, 9-fluorene methanol (29.5 g, 150 mmole) was added and stirring was continued. After 16 hours, the reaction mixture was diluted with 1200 mL ethyl acetate and extracted with 300 mL each of water, 1 M aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo. The resulting oil was dissolved in 500 mL dichloromethane and treated with 100 mL of a 4.0M solution of hydrochloric acid in dioxane. After 12 hours, the title compound was precipitated by pouring the reaction mixture into ether (1000 mL) with vigorous stirring. The precipitate was filtered and dried in vacuo to provide 35 g (73% yield) of the title compound as an off-white powder.

Workup

  1. waitAfter 16 hours
  2. extractionextracted with 300 mL each of water, 1 M aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. dissolutionThe resulting oil was dissolved in 500 mL dichloromethane
  7. additiontreated with 100 mL of a 4.0M solution of hydrochloric acid in dioxane
  8. waitAfter 12 hours
  9. customthe title compound was precipitated
  10. additionby pouring the reaction mixture into ether (1000 mL) with vigorous stirring
  11. filtrationThe precipitate was filtered
  12. customdried in vacuo

Sources & evidence

ORD record
ord-f9bc15262fdb481c936390da329f0620
Source dataset
uspto-grants-2000_02
Patent number
US06025472

Linked notes

Loading…