Hydrochloric Acid → Carbamic acid, (4-oxobutyl)-, 9H-fluoren-9-ylmethyl ester

HRID 1778604Notes

Reaction equation

HRID 1778604 reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][CH2:7][NH:8][C:9]([O:11][CH2:12][CH:13]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])C.Cl>O1CCOCC1>[C:9]([NH:8][CH2:7][CH2:6][CH2:5][CH:4]=[O:3])([O:11][CH2:12][CH:13]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58520747HCID 58520747, compound

Product 1

HCID 22184307Carbamic acid, (4-oxobutyl)-, 9H-fluoren-9-ylmethyl esterYield 98,000%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirring solution of N-Fmoc-4-amino-butyraldehyde diethyl acetal (0.050 mmol) in 1,4-dioxane (100 mL) was added aq. HCl (100 ml, 1:1 v/v, H2O: conc. HCl) and the reaction progress was monitored by MS. Upon completion, the organic solvent was removed by rotary evaporation, and the aqueous layer was extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with 5% NaHCO3 (2×75 mL), brine (75 mL), dried over Na2SO4, filtered and concentrated to dryness to yield the desired N-Fmoc-4-amino-butyraldehyde (15.35 g, 0.049 mol, 90.0% yield), which was carried through to the next step without further purification: MS m/e [M+Na]+ calcd 332.1, found 332.0.

Workup

  1. customUpon completion, the organic solvent was removed by rotary evaporation
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×200 mL)
  3. washThe combined organic layers were washed with 5% NaHCO3 (2×75 mL), brine (75 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c7deedc25632463298b61f981c37674b
Source dataset
uspto-grants-2016_02
Patent number
US09266919B2

Reaction notes

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