[Methyl-(toluene-4-sulfonyl)-amino]-acetic acid → N-(toluene-4-sulfonyl)sarcosyl-N-methylphenylalanine methyl ester

HRID 1374606Notes

Reaction equation

HRID 1374606 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([S:7]([N:10]([CH2:12][C:13]([OH:15])=O)[CH3:11])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:17][O:18][C:19](=[O:30])[C@H:20]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH:21][CH3:22]>>[CH3:17][O:18][C:19](=[O:30])[C@H:20]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[N:21]([C:13](=[O:15])[CH2:12][N:10]([S:7]([C:4]1[CH:3]=[CH:2][C:1]([CH3:16])=[CH:6][CH:5]=1)(=[O:8])=[O:9])[CH3:11])[CH3:22]

Participants

3

Reactant 2

HCID 802555[Methyl-(toluene-4-sulfonyl)-amino]-acetic acidHCID 7021804methyl (2S)-2-(methylamino)-3-phenylpropanoate

Product 1

HCID 54204174N-(toluene-4-sulfonyl)sarcosyl-N-methylphenylalanine methyl ester

Procedure

N-(Toluene-4-sulfonyl)sarcosine was coupled to N-methyl-L-phenylalanine methyl ester using the procedure described in Method 3 to give N-(toluene-4-sulfonyl)sarcosyl-N-methylphenylalanine methyl ester. The title compound was prepared via hydrolysis of the methyl ester using LiOH in THF/water. Proton and carbon NMR analysis indicated a mixture of amide bond rotomers in about a 65:35 ratio.

Sources & evidence

ORD record
ord-73435f5d5eb44710b808f20570990970
Source dataset
uspto-grants-2007_01
Patent number
US07166580B2

Reaction notes

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