Iodine → HCID 117736433, compound

HRID 1482306Notes

Reaction equation

[C:1](SSC(C)(C)C)(C)(C)C.II.[S:13]([CH:37]([CH2:55]N=[N+]=[N-])[CH2:38][C@H](NC(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[S:14][CH:15]([CH2:33][N:34]=[N+:35]=[N-:36])[CH2:16][C@H:17]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>>[C:21]([O:20][C:18](=[O:19])[C@@H:17]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])[CH2:16][CH:15]([S:14][S:13][C:37]([CH3:1])([CH3:55])[CH3:38])[CH2:33][N:34]=[N+:35]=[N-:36])([CH3:23])([CH3:24])[CH3:22]

Participants

Reactant 3

HCID 807Iodine

HCID 66060t-Butyl disulfide

HCID 89668705HCID 89668705, compound2×

Product 1

HCID 117736433HCID 117736433, compoundYield 82%

Conditions

Temperature: 60 °C

Procedure

Di-tert-butyl disulfide (5.67 ml, 29.4 mmol) and iodine (57 mg, 0.226 mmol) were added to (2S,2'S)-di-tert-butyl 4,4′-disulfanediylbis(5-azido-2-((tert-butoxycarbonyl)amino)pentanoate) (Compound 38) (312 mg, 0.452 mmol), and the mixture was stirred at 60° C. for 18 hours. The reaction solution was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate) to afford (S)-5-azido-2-tert-butoxycarbonylamino-4-tert-butyldisulfanyl-pentanoic acid tert-butyl ester (Compound 39) (161 mg, 81%).

Workup

customThe reaction solution was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-e9243b885e04434ab2e5a6f7ad64fdc8
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409952B2

Reaction notes

Loading…