1,4-Diiodobutane → HCID 58331116, compound

HRID 625826Notes

Reaction equation

[C:1]([NH:8][C@H:9]([C:16]([O:18][CH3:19])=[O:17])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[I:30][CH2:31][CH2:32][CH2:33][CH2:34]I>O1CCCC1>[C:4]([O:3][C:1]([NH:8][C@@H:9]([CH2:10][C@H:11]([CH2:34][CH2:33][CH2:32][CH2:31][I:30])[C:12]([O:14][CH3:15])=[O:13])[C:16]([O:18][CH3:19])=[O:17])=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

Conditions

Temperature: -70 °C

Procedure

5.51 g (20 mmol) of dimethyl Boc-glutamate were dissolved in 60 ml of tetrahydrofuran and cooled to −70° C. Over a period of one hour, 44 ml (44 mmol) of a 1M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran were added dropwise at this temperature, and the mixture was stirred at −70° C. for 2 hours. 18.60 g (60 mmol) of 1,4-diiodobutane were then added dropwise, and after 2 h at this temperature the cooling bath is removed and 100 ml of 2N hydrochloric acid and 300 ml of ethyl acetate were added. The organic phase was separated off, washed with water until neutral, dried over sodium sulphate and filtered, and the filtrate was concentrated. The crude product obtained in this manner was chromatographed on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

Workup

customafter 2 h at this temperature the cooling bath is removed
addition100 ml of 2N hydrochloric acid and 300 ml of ethyl acetate were added
customThe organic phase was separated off
washwashed with water until neutral,
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-06de5d5d47034f729dc10913f8ae03c3
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09308282B2

Reaction notes

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