Picolyl chloride → HCID 69200917, compound

HRID 2250980Notes

Reaction equation

C[O:2][C:3](=[O:23])[CH:4]([NH:15]C(OC(C)(C)C)=O)[CH2:5][C:6]1[CH:11]=[C:10]([Br:12])[C:9]([OH:13])=[C:8]([Br:14])[CH:7]=1.Cl[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1>>[CH2:3]([NH+:27]([CH2:26][CH3:31])[CH2:28][CH3:29])[CH3:4].[NH2:15][CH:4]([CH2:5][C:6]1[CH:7]=[C:8]([Br:14])[C:9]([O:13][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)=[C:10]([Br:12])[CH:11]=1)[C:3]([O-:2])=[O:23]

Participants

Reactant 2

HCID 23393Picolyl chloride

HCID 14631438HCID 14631438, compound

Product 1

HCID 69200917HCID 69200917, compoundYield 21%

Procedure

Methyl-2-tert-butoxycarbonylamino-3-(3,5-dibromo-4-hydroxyphenyl)propionate (0.035 mmol) was coupled with 2-chloromethylpyridine and hydrolyzed using the method described in “General procedure for the preparation of Examples 8-22”. This gave 21% yield of 2-amino-3-[3,5-dibromo-4-(pyridin-2-ylmethoxy)phenyl]propionate triethylammonium. LC/MS (electrospray): m/z 429 (M−1).

Workup

customdescribed in “General procedure for the preparation of Examples 8-22”

Sources & evidence

ORD record: ord-bded5680f5ca4cb0b5da3d599fad6792
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319096B2

Reaction notes

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