N-Iodosuccinimide → HCID 58972246, compound

HRID 20336Notes

Reaction equation

[C:1]([O:5][C:6](=[O:34])[NH:7][C@H:8]([CH2:32][OH:33])[C@@H:9]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@@H:10]([NH:20][C:21](=[O:23])[CH3:22])[CH2:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:35][C:36]([CH3:43])([CH3:42])[CH2:37][CH2:38][O:39][CH:40]=[CH2:41].[I:44]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:34])[NH:7][C@H:8]([CH2:32][O:33][CH:40]([O:39][CH2:38][CH2:37][C:36]([CH3:43])([CH3:42])[CH3:35])[CH2:41][I:44])[C@@H:9]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@@H:10]([NH:20][C:21](=[O:23])[CH3:22])[CH2:11][C:12]1[CH:13]=[C:14]([F:19])[CH:15]=[C:16]([F:18])[CH:17]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

Dissolve [(1R,2S,3S)-3-acetylamino-2-benzyloxy-4-(3,5-difluorophenyl)-1-hydroxymethyl-butyl]-carbamic acid tert-butyl ester (0.52 g, 1.09 mmol) and 3,3-dimethyl-1-vinyloxybutane (0.15 g, 1.20 mmol) in acetonitrile (6 mL) and add N-iodosuccinimide (0.27 g, 1.20 mmol) at room temperature. Heat in oil bath at 80° C. for 2 hours 45 minutes. Cool to room temperature, dilute with ethyl acetate, wash with water or 10% aqueous sodium thiosulfate, saturated aqueous sodium chloride, concentrate and purify (silica gel chromatography, eluting with 10:90 to 30:70 ethyl acetate:hexanes) to give the title compound (0.557 g, 70% yield).

Workup

temperatureCool to room temperature
washwash with water or 10% aqueous sodium thiosulfate, saturated aqueous sodium chloride
concentrationconcentrate
custompurify
wash(silica gel chromatography, eluting with 10:90 to 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record: ord-32bae15daaca480c88a75a7c3cda7cbd
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745438B2

Reaction notes

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