Isopropyl iodide → HCID 67130884, compound

HRID 1746594Notes

Reaction equation

HRID 1746594 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[CH:26]([CH3:28])[CH3:27]>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]([CH:26]([CH3:28])[CH3:27])[CH:14]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 14798Sodium HydroxideHCID 83169N-tert-Butoxycarbonyl-L-tryptophan

Product 1

HCID 67130884HCID 67130884, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

The same procedures as in Example 137 were carried out from sodium hydroxide (2.8 g), methylene chloride (100 mL), N-tert-butoxycarbonyl-L-tryptophan (6.0 g), 2-iodopropane (9.8 mL), and tetra-n-butylammonium hydrogensulfate (0.7 g), to give the captioned compound (1.6 g, 23%) as an oily product.

Sources & evidence

ORD record
ord-3423bb85865849bf8ec628af27113572
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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