[Methyl-(toluene-4-sulfonyl)-amino]-acetic acid → N-(toluene-4-sulfonyl)sarcosyl-Nepsilon-Boc-L-lysine methyl ester

HRID 1182043Notes

Reaction equation

HRID 1182043 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.Cl.[CH3:18][O:19][C:20](=[O:35])[C@H:21]([CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[NH2:22]>>[CH3:18][O:19][C:20](=[O:35])[C@H:21]([CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[NH:22][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]

Participants

3

Reactant 2

HCID 802555[Methyl-(toluene-4-sulfonyl)-amino]-acetic acidHCID 16218818L-Lysine, N6-[(1,1-dimethylethoxy)carbonyl]-, methyl ester, hydrochloride (1:1)

Product 1

HCID 54444302N-(toluene-4-sulfonyl)sarcosyl-Nepsilon-Boc-L-lysine methyl ester

Procedure

N-(Toluene-4-sulfonyl)sarcosine was coupled to Nε-Boc-L-lysine methyl ester hydrochloride using the procedure described in Method 3 to give N-(toluene-4-sulfonyl)sarcosyl-Nε-Boc-L-lysine methyl ester. The title compound was prepared via hydrolysis of the methyl ester using LiOH in THF/water.

Sources & evidence

ORD record
ord-4009f3eb1220403a906047aa1b2c050e
Source dataset
uspto-grants-2007_10
Patent number
US07288526B2

Reaction notes

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