9-Fluorenylmethyl chloroformate → 9-Fluorenylmethyl carbazate

HRID 1828768Notes

Reaction equation

HRID 1828768 reaction equation
[C:1]([NH:8][NH2:9])([O:3][C:4](C)(C)[CH3:5])=[O:2].CCN(C(C)C)C(C)C.C(Cl)(OCC1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)=O>C(Cl)Cl>[CH:34]1[C:35]2[CH:5]([CH2:4][O:3][C:1]([NH:8][NH2:9])=[O:2])[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]=2[CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 343679-Fluorenylmethyl chloroformateHCID 70091tert-Butyl carbazateHCID 81531Diisopropylethylamine

Product 1

HCID 1618839-Fluorenylmethyl carbazateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Boc-hydrazine (10.0 g, 75.6 mmol) and DIPEA (12.95 ml, 75.6 mmol) were dissolved in dry CH2Cl2 (200 ml) and cooled to 0° C. FmocCl (19.6 g, 75.8 mmol), dissolved in dry CH2Cl2 (100 ml), was then added over the course of 30 minutes, and the mixture was stirred overnight at room temperature. The organic phase was extracted with water (200 ml) and evaporated to a volume of about 100 ml. Trifluoroacetic acid (100 ml) was then carefully added at 0° C., and the mixture was stirred for 1.5 hours. The product was precipitated by careful addition of saturated Na2CO3 solution (300 ml) and dried, giving a colourless solid (18.02 g, 70.8 mmol, 94%).

Workup

  1. additionwas then added over the course of 30 minutes
  2. extractionThe organic phase was extracted with water (200 ml)
  3. customevaporated to a volume of about 100 ml
  4. additionTrifluoroacetic acid (100 ml) was then carefully added at 0° C.
  5. stirringthe mixture was stirred for 1.5 hours
  6. customThe product was precipitated by careful addition of saturated Na2CO3 solution (300 ml)
  7. customdried

Sources & evidence

ORD record
ord-b335b15699194f73b3974af43904ae49
Source dataset
uspto-grants-2006_06
Patent number
US07060707B2

Reaction notes

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