Cyclopropanesulfonyl chloride → Ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentanecarboxylate

HRID 1969503Notes

Reaction equation

HRID 1969503 reaction equation
[CH:1]1([S:4]([NH:7][C@@H:8]2[CH2:12][C@H:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C@H:10]([CH2:18][CH3:19])[CH2:9]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.NC1CC(C(OCC)=O)C(CC)C1.C1(S(Cl)(=O)=O)CC1>>[CH:1]1([S:4]([NH:7][CH:8]2[CH2:12][CH:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]([CH2:18][CH3:19])[CH2:9]2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 2760919Cyclopropanesulfonyl chlorideHCID 58009905Ethyl 4-amino-2-ethylcyclopentanecarboxylateHCID 58010129(1S,2R,4S)-ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentanecarboxylate

Product 1

HCID 58558091Ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentanecarboxylate

Procedure

The precursor to Preparation #Z.1, (1S,2R,4S)-ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentane-carboxylate, was prepared (as shown in Scheme B) by initially reacting ethyl 4-amino-2-ethylcyclopentanecarboxylate (Preparation #Y.1) with the commercially available cyclopropanesulfonyl chloride, following the conditions given in General Procedure K, to give ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentane-carboxylate as a mixture of stereoisomers. This mixture of stereoisomers is separated as described in General Procedure AA, using the conditions from Method 1 in Table 2, to give the precursor to Preparation #Z.1, (1S,2R,4S)-ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentane-carboxylate as a single enantiomer with a retention time of 9.5 minutes and a negative optical rotation. The reaction sequence to synthesize the precursor to Preparation #Z.1, (1S,2R,4S)-ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentane-carboxylate, (detailed above) is consequently translated in the preparations and examples section to: (1S,2R,4S)-ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentane-carboxylate (prepared using K from Preparation #Y.1 and cyclopropanesulfonyl chloride, AA [Table 2, Method 1, Rt=9.5 min, or =negative]). Hence the Preparation #Z.1 would be written as: Preparation #Z.1 was prepared from (1S,2R,4S)-ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentane carboxylate (prepared using K from Preparation #Y.1 and cyclopropanesulfonyl chloride, AA [Table 2, Method 1, Rt=9.5 min, or =negative]) using General Procedure Z.

Sources & evidence

ORD record
ord-6119ad72ca41481a888982ee6e6ef5ec
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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