4-Toluenesulfonyl chloride → HCID 86621618, compound

HRID 2246938Notes

Reaction equation

HRID 2246938 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:13](=[O:14])[CH2:12][C:11](=[O:15])[CH2:10][C@H:9]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>CCOC(C)=O.CCCCCCC>[C:1]([O:5][C:6]([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([O:15][S:32]([C:29]2[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=2)(=[O:34])=[O:33])[CH2:10][C@H:9]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68442963HCID 68442963, compound

Product 1

HCID 86621618HCID 86621618, compound

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

Similar to example 24c, 9.43 g of (2S)-4,6-dioxo-piperidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester [176436-10-5] are reacted with p-toluene sulfonyl chloride to afford the title compound as a yellow oil Rf=0.64 (EtOAc-heptane 1:1); Rt=5.20.

Sources & evidence

ORD record
ord-a5701c1790254c3fa8f9faa19f472ccb
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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