Tetrahydrofuran → (Methyl-{4-[3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-benzoyl}-amino)-acetic acid methyl ester

HRID 1617713Notes

Reaction equation

HRID 1617713 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([C:9](=[O:28])[CH2:10][CH:11]([C:19]2[CH:27]=[CH:26]C(C(O)=O)=CC=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:3]1.Cl.[CH3:30][O:31][C:32](=[O:36])[CH2:33][NH:34][CH3:35].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[O:64]1[CH2:68][CH2:67][CH2:66][CH2:65]1>>[CH3:30][O:31][C:32](=[O:36])[CH2:33][N:34]([CH3:35])[C:68](=[O:64])[C:67]1[CH:26]=[CH:27][C:19]([CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH2:10][C:9]([C:4]2[CH:5]=[CH:6][C:7](=[O:8])[N:2]([CH3:1])[CH:3]=2)=[O:28])=[CH:65][CH:66]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 670155254-[3-(1-Methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-benzoic acid

Product 1

HCID 67015556(Methyl-{4-[3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-benzoyl}-amino)-acetic acid methyl ester

Procedure

In analogy to example 207, step 2, 4-[3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-benzoic acid (example 207, step 1) was coupled with sarcosine methyl ester hydrochloride using BOP reagent in tetrahydrofuran to give the title compound as a colorless solid, MS (ESI+): m/z=461.3 [M+H]+

Sources & evidence

ORD record
ord-5dd6bd1c300746e78a5b9a6e425d37f7
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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