Benzyl Bromide → HCID 67130653, compound

HRID 1746606Notes

Reaction equation

HRID 1746606 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].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH2:25]([N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([CH2:12][C@@H:11]([C:22]([O:24][CH2:13][C:21]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:23])[NH:10][C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])=[CH:14]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 83169N-tert-Butoxycarbonyl-L-tryptophan

Product 1

HCID 67130653HCID 67130653, compoundYield 77%

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), benzyl bromide (20 mL), and tetra-n-butylammonium hydrogensulfate (1.1 g), to give the captioned compound (12.2 g, 77%) as an oily product.

Sources & evidence

ORD record
ord-7f073b50ad964f42b3a938170297ce67
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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