4-Toluenesulfonyl chloride → methyl 7-(N-benzyloxycarbonylamino)-3-p-toluenesulfonyloxy-2-phenylheptanoate

HRID 2392934Notes

Reaction equation

HRID 2392934 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([OH:29])[CH:17]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([O:20][CH2:21]C)=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C1C=CC=CN=1)C.[C:39]1([CH3:49])[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([O:29][S:45]([C:42]1[CH:43]=[CH:44][C:39]([CH3:49])=[CH:40][CH:41]=1)(=[O:47])=[O:46])[CH:17]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 218852-DimethylaminopyridineHCID 18980744ethyl 7-(N-benzyloxycarbonylamino)-3-hydroxy-2-phenylheptanoate

Product 1

HCID 18980749methyl 7-(N-benzyloxycarbonylamino)-3-p-toluenesulfonyloxy-2-phenylheptanoateYield 61.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The same procedures as in Example 30 were performed except that 27.2 g (70.4 mmol) of methyl 7-(N-benzyloxycarbonylamino)-3-hydroxy-2-phenylheptanoate obtained in Example 9 was dissolved in 136 ml of pyridine; 1.27 g (10.39 mmol) of dimethylaminopyridine was added; and 20.1 g (105.6 mmol) of p-toluenesulfonyl chloride was added; to prepare the target compound as a pale yellow oil in an amount 23.5 g at a yield of 61.8%. The analytical results on the target compound are given below.

Workup

  1. customThe analytical results on the target compound

Sources & evidence

ORD record
ord-1229274e77f248ae97f0ebffc6435092
Source dataset
uspto-grants-1998_09
Patent number
US05801271

Reaction notes

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