Acetic Acid → N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine

HRID 403007Notes

Reaction equation

C([O:3][C:4](=[O:38])[C@H:5]([CH2:14][C:15]1[C:20]([I:21])=[CH:19][C:18]([O:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:17]([O:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:16]=1)[NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])C.[OH-].[Li+].C(O)(=O)C>C1COCC1.O>[C:10]([O:9][C:7]([NH:6][C@H:5]([C:4]([OH:38])=[O:3])[CH2:14][C:15]1[C:20]([I:21])=[CH:19][C:18]([O:22][C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])=[C:17]([O:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:16]=1)=[O:8])([CH3:11])([CH3:12])[CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

The iodo derivative 17 (3.5 mmol) (prepared as shown in FIG. 6) was dissolved in 40 mL of THF and cooled in an ice bath (0° C.) and a solution of lithium hydroxide (7.0 mmol) in 12 mL of water was added dropwise under argon. The resulting mixture was stirred at 0° C. for 4 h and then 2 h at room temperature. The reaction mixture was then neutralized with acetic acid to pH 5 and extracted with ethyl acetate. The organic phase was dried using Na2SO4, filtered and evaporated to dryness to provide an oil which was purified by silical gel column chromatography resulting in N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine (23).

Workup

custom2 h
customat room temperature
extractionextracted with ethyl acetate
customThe organic phase was dried
filtrationfiltered
customevaporated to dryness
customto provide an oil which
customwas purified by silical gel column chromatography
customresulting in N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine (23)

Sources & evidence

ORD record: ord-e3264ddc1553450cb2aa5d82cebe6799
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742139B2

Reaction notes

Loading…