Glycine, N-methyl-, hydrochloride (1:1) → HCID 69423893, compound

HRID 1269558Notes

Reaction equation

HRID 1269558 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:22][C:23]([OH:25])=O)[CH:5]=[C:6]([Cl:21])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])=[CH:11][CH:10]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:50][NH:51][CH2:52][C:53]([OH:55])=[O:54]>CN(C)C=O.C(N(CC)CC)C>[CH3:50][N:51]([C:23](=[O:25])[CH2:22][C:4]1[CH:5]=[C:6]([Cl:21])[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:20])[CH:17]([CH3:18])[CH3:19])=[CH:11][CH:10]=2)=[C:2]([Cl:1])[CH:3]=1)[CH2:52][C:53]([OH:55])=[O:54]

Participants

7

Reactant 4

HCID 69483Glycine, N-methyl-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 9970123HCID 9970123, compound

Product 1

HCID 69423893HCID 69423893, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 3,5-dichloro-4-(4-isobutyramidophenoxy)phenylacetic acid (70 mg), 3-ethyl-1-[3-(dimethylamino)propyl]carbodiimide hydrochloride (49 mg), 1-hydroxybenzo-triazole hydrate, (45 mg) in dimethyl formamide (2 mL) was stirred at room temperature for 0.5 hours followed by addition of a solution of methyl glycine hydrochloride (46 mg) and triethylamine (56 mg) in dimethylformamide (1 mL). After stirring for one day, the reaction mixture was concentrated. The residue was purified by HPLC as described for Examples 33–90, to give methyl N-[3,5-dichloro-4-(4-isobutyramidophenoxy)phenylacetyl]glycine. The ester was hydrolyzed using the method described in Example 1(i) and purified as above, to give 25 mg (31%) of N-[3,5-dichloro-4-(4-isobutyramidophenoxy)phenylacetyl]glycine, m/z 439.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-5df325e4216f46a7892ac262d27b6bc0
Source dataset
uspto-grants-2007_04
Patent number
US07199265B2

Reaction notes

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