Dimethylformamide → (9H-Fluoren-9-yl)methyl 2-oxoethylcarbamate

HRID 1726920Notes

Reaction equation

HRID 1726920 reaction equation
CN(C=O)C.[C:6]([NH:23][CH2:24][C:25](O)=[O:26])([O:8][CH2:9][CH:10]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7].C(N=C=NC(C)C)(C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH:13]1[CH:12]=[C:11]2[CH:10]([CH2:9][O:8][C:6]([NH:23][CH2:24][CH:25]=[O:26])=[O:7])[C:22]3[C:17]([C:16]2=[CH:15][CH:14]=1)=[CH:18][CH:19]=[CH:20][CH:21]=3

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 12734DiisopropylcarbodiimideHCID 93124Fmoc-Gly-OH

Product 1

HCID 10858926(9H-Fluoren-9-yl)methyl 2-oxoethylcarbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Wang resin (70 g, 119 mmol, PL-Wang, Polymer Labs, 1.7 mmol/g.) was swollen in 550 mL of methylene chloride and 100 mL of DMF and stirred for 30 min with an overhead stirrer. 71 g (238 mmol) of FMOC-glycine were added, followed by 60 g (476 mmol) of diisopropylcarbodiimide and 2.4 g (19.7 mmol) of 4-dimethylaminopyridine. The reaction was stirred for 3.5 h at room temperature, the resin was filtered, washed with alternating methanol and methylene chloride and dried in a vacuum oven.

Workup

  1. filtrationthe resin was filtered
  2. washwashed with alternating methanol and methylene chloride
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-65454cf26d714c4abffdc1fd68610bcc
Source dataset
uspto-grants-2009_02
Patent number
US07494996B2

Reaction notes

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