Potassium Iodide → Nalpha-(9-fluorenylmethoxycarbonyl)-O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester

HRID 1275749Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:23][OH:24])[NH:5][C:6]([O:8][CH2:9][CH:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[C:35]1([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:47]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[C:41]2[C:36]1=[CH:37][CH:38]=[CH:39][CH:40]=2>C(#N)C>[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:23][O:24][C:35]1([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:47]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[C:41]2[C:36]1=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:5][C:6]([O:8][CH2:9][CH:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=2[C:17]2[C:22]1=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:7]

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of 0.17 g (0.5 mmol) Nα -(9-fluorenylmethoxycarbonyl)-L-serine methyl ester, 0.043 g (0.6 mmol) potassium carbonate and 0.083 g (0.5 mmol) potassium iodide in acetonitrile (2 mL) was added 0.16 g (0.5 mmol) of 9-bromo-9-phenyl-9H-fluorene (Aldrich), and the mixture stirred at 40° C. for 2 h. Filtration and removal of the solvent under vacuo gave the crude Nα -(9-fluorenylmethoxycarbonyl)-O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester which was subjected to the Fmoc deprotection in Step 2 without further purification.

Workup

filtrationFiltration and removal of the solvent under vacuo

Sources & evidence

ORD record: ord-acb2451a8423426a847ebb7c0c5b9c6a
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06162824

Reaction notes

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