p-Toluenesulfonate → HCID 18646530, compound

HRID 2248521Notes

Reaction equation

HRID 2248521 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([OH:15])=O)=[O:8])=[CH:5][CH:4]=1)#[N:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH2:32][C@H:33]([C:42]([O:44][CH3:45])=[O:43])[CH2:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38]>CN(C=O)C>[CH3:45][O:44][C:42](=[O:43])[C@H:33]([CH2:34][C:35]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:41])[NH:32][C:13](=[O:15])[C:12]1[CH:16]=[CH:17][CH:18]=[C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:20][CH:19]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 85570p-ToluenesulfonateHCID 7016379HCID 7016379, compoundHCID 10423016HCID 10423016, compound

Product 1

HCID 18646530HCID 18646530, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

m-(p-Cyanobenzamido)benzoic acid is activated in the same manner as described under a) and coupled with the p-toluenesulphonate of H-Asp(OtBu)OMe in DMF at room temperature. There is isolated 3-(t-butoxycarbonyl)-N-[m-(p-cyanobenzamido)benzoyl]-L-alanine methyl ester in the form of colourless crystals. Yield: 65%, m.p. 83°-84° C. (hexane).

Sources & evidence

ORD record
ord-7806ce1663654cac9a69f5269443b2fe
Source dataset
uspto-grants-1991_08
Patent number
US05039805

Reaction notes

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