Glycine, N-methyl-, hydrochloride (1:1) → HCID 10208081, compound

HRID 1269559Notes

Reaction equation

HRID 1269559 reaction equation
ClC1C=C(CC(O)=O)C=C(Cl)C=1OC1C=CC(NC(=O)C(C)C)=C(Br)C=1.Cl.CNCC(O)=O.C[N:35]([C:40](=[O:64])[CH2:41][C:42]1[CH:47]=[C:46]([Cl:48])[C:45]([O:49][C:50]2[CH:55]=[CH:54][C:53]([NH:56][C:57](=[O:61])[CH:58]([CH3:60])[CH3:59])=[C:52]([Br:62])[CH:51]=2)=[C:44]([Cl:63])[CH:43]=1)[CH2:36][C:37]([OH:39])=[O:38]>>[Cl:48][C:46]1[CH:47]=[C:42]([CH2:41][C:40]([NH:35][CH2:36][C:37]([OH:39])=[O:38])=[O:64])[CH:43]=[C:44]([Cl:63])[C:45]=1[O:49][C:50]1[CH:55]=[CH:54][C:53]([NH:56][C:57](=[O:61])[CH:58]([CH3:60])[CH3:59])=[C:52]([Br:62])[CH:51]=1

Participants

4

Reactant 3

HCID 69483Glycine, N-methyl-, hydrochloride (1:1)HCID 9933993HCID 9933993, compoundHCID 69426772HCID 69426772, compound

Product 1

HCID 10208081HCID 10208081, compoundYield 22%

Procedure

3,5-Dichloro-4-(3-bromo-4-isobutyramidophenoxy)phenylacetic acid (56 mg) was coupled with methyl glycine hydrochloride (31 mg) using the method described in Example 9. This gave methyl N-[3,5-dichloro-4-(3-bromo-4-isobutyramidophenoxy)phenylacetyl]-glycine, which was hydrolyzed using the method described in Example 1(i) and purified as in Example 9, to give 14 mg (22%) of N-[3,5-dichloro-4-(3-bromo-4-isobutyramidophenoxy)phenylacetyl]glycine, m/z 518.

Workup

  1. custompurified as in Example 9

Sources & evidence

ORD record
ord-2b119bfa0b2f4c4c97f921aac5c25df9
Source dataset
uspto-grants-2007_04
Patent number
US07199265B2

Reaction notes

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