Diisopropylcarbodiimide → HCID 86704391, compound

HRID 1408300Notes

Reaction equation

HRID 1408300 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][C:26]([OH:28])=[O:27])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.O[N:30]1[C:34](=[O:35])[CH2:33][CH2:32][C:31]1=[O:36].CC(C)N=C=NC(C)C>C1COCC1>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][C:26]([O:28][N:30]3[C:34](=[O:35])[CH2:33][CH2:32][C:31]3=[O:36])=[O:27])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 27560921-(9H-Fluoren-9-yl)-3-oxo-2,7,10-trioxa-4-azadodecan-12-oic acid

Product 1

HCID 86704391HCID 86704391, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[2-(2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethoxy)ethoxy]acetic acid (185 mg, 0.480 mmol) and N-hydroxysuccinimide (110 mg, 0.956 mmol) were dissolved in anhydrous THF (1.5 mL). DIC was added dropwise to the solution at r.t., leading to the precipitation of a white solid. After 2 h, the reaction mixture was filtrated through a PTFE membrane filter (0.2 μm), and the solvent was removed. The crude product was redissolved in Et2O. The organic phase was washed with aq. NaHCO3 and 0.5 M aq. HCl. The organic layer was dried over Na2SO4, and the solvent was removed. The crude product was dissolved in CH2Cl2, and the solution was filtrated. After removal of the solvent, the crude product 39 (210 mg) was used in the synthesis of 40 without further purification.

Workup

  1. customleading to the precipitation of a white solid
  2. filtrationthe reaction mixture was filtrated through a PTFE membrane
  3. filtrationfilter (0.2 μm)
  4. customthe solvent was removed
  5. dissolutionThe crude product was redissolved in Et2O
  6. washThe organic phase was washed with aq. NaHCO3 and 0.5 M aq. HCl
  7. dry with materialThe organic layer was dried over Na2SO4
  8. customthe solvent was removed
  9. dissolutionThe crude product was dissolved in CH2Cl2
  10. filtrationthe solution was filtrated
  11. customAfter removal of the solvent
  12. customthe crude product 39 (210 mg) was used in the synthesis of 40 without further purification

Sources & evidence

ORD record
ord-d5d8c9c9c6c941a99efc6218c7e2607b
Source dataset
uspto-grants-2014_12
Patent number
US08921328B2

Reaction notes

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