Butyl iodide → HCID 67130666, compound

HRID 1746595Notes

Reaction equation

HRID 1746595 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]([C:22]([OH:24])=[O:23])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].I[CH2:26][CH2:27][CH2:28][CH3:29]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:3]([O:7][C:8]([NH:10][C@H:11]([C:22]([OH:24])=[O:23])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:26][CH2:27][CH2:28][CH3:29])[CH:14]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 10962Butyl iodideHCID 14798Sodium HydroxideHCID 83169N-tert-Butoxycarbonyl-L-tryptophan

Product 1

HCID 67130666HCID 67130666, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

The same procedures as in Example 137 were carried out from sodium hydroxide (4.6 g), methylene chloride (160 mL), N-tert-butoxycarbonyl-L-tryptophan (10.0 g), 1-iodobutane (19 mL), and tetra-n-butylammonium hydrogensulfate (1.1 g), to give the captioned compound (6.2 g, 52%) as an oily product.

Sources & evidence

ORD record
ord-d0aa9f4d07684d509dcc56e6bfb59fba
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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