9-Fluorenylmethyl chloroformate → (9H-Fluoren-9-yl)methyl decyl(2-oxoethyl)carbamate

HRID 966458Notes

Reaction equation

HRID 966458 reaction equation
C(CCCCCCCCCCN)C=C.C(N(CC)C(C)C)(C)C.ClC([O:27][CH2:28][CH:29]1C2C=CC=CC=2C2C1=CC=CC=2)=O.[C:42]([NH:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69]CC=C)([O:44][CH2:45][CH:46]1[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[C:52]2[C:47]1=[CH:48][CH:49]=[CH:50][CH:51]=2)=[O:43]>ClCCl>[C:42]([N:59]([CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH3:69])[CH2:29][CH:28]=[O:27])([O:44][CH2:45][CH:46]1[C:47]2[C:52](=[CH:53][CH:54]=[CH:55][CH:48]=2)[C:51]2[C:58]1=[CH:57][CH:56]=[CH:49][CH:50]=2)=[O:43]

Participants

6

Reactant 4

HCID 343679-Fluorenylmethyl chloroformate4×HCID 81531DiisopropylethylamineHCID 53801489HCID 53801489, compoundHCID 69732531HCID 69732531, compound

Product 1

HCID 10070832(9H-Fluoren-9-yl)methyl decyl(2-oxoethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

A three-necked, 500 mL round bottom flask equipped with a thermometer, mechanic stirrer and an addition funnel was purged with nitrogen and charged with N-allyldecylamine (˜0.11 mol) in dichloromethane from step a (210 mL) and N,N-diisopropylethylamine (20.0 mL, 14.8 g, 0.113 mol). The mixture was cooled in a 5° C. ice bath and a solution of 9-fluorenylmethyl chloroformate (25.6 g, 0.099 mol) dissolved in dichloromethane (50 mL) was added dropwise (total volume approximately 330 mL). The reaction was exothermic and the internal temperature was controlled below 10° C. throughout the 9-fluorenylmethyl chloroformate addition. The reaction mixture was warmed to 21° C. when the addition was finished, and monitored by the disappearance of 9-fluorenylmethyl chloroformate and the formation of N-FMOC-N-allyldecylamine using HPLC (retention time for FMOC-chloride=3.08 min; retention time for product=7.96 min). The reaction mixture was washed with 0.01 N HCl (100 mL). The organic layer was collected and used without further purification.

Workup

  1. customA three-necked, 500 mL round bottom flask equipped with a thermometer, mechanic stirrer and an addition funnel
  2. customwas purged with nitrogen
  3. additionwas added dropwise (total volume approximately 330 mL)
  4. temperatureThe reaction mixture was warmed to 21° C. when
  5. additionthe addition
  6. washThe reaction mixture was washed with 0.01 N HCl (100 mL)
  7. customThe organic layer was collected
  8. customused without further purification

Sources & evidence

ORD record
ord-a433cb9279ff41d8b77458c64a7f7675
Source dataset
uspto-grants-2005_10
Patent number
US06951963B2

Reaction notes

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