1,2-Ethanedithiol → 7-benzyloxycarbonyl-1,4-dithia-7-azaspiro [4.4]nonane-8(S)carboxylic acid, ethyl ester

HRID 2226406Notes

Reaction equation

HRID 2226406 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][C:19](=O)[CH2:18][C@H:12]1[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([SH:25])[CH2:23][SH:24]>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[C@H:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:18][C:19]2([S:25][CH2:22][CH2:23][S:24]2)[CH2:20]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 109021,2-EthanedithiolHCID 14540986Ethyl (S)-1-Cbz-4-oxopyrrolidine-2-carboxylate

Product 1

HCID 145409887-benzyloxycarbonyl-1,4-dithia-7-azaspiro [4.4]nonane-8(S)carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

As described in Example 23, react 1-benzyloxycarbonyl-4-keto-(S)-proline, ethyl ester (prepared from the acid by esterification in ethanol) with 1,2-ethanedithiol to obtain 7-benzyloxycarbonyl-1,4-dithia-7-azaspiro [4.4]nonane-8(S)carboxylic acid, ethyl ester, a yellow oil [α]D26 -21.0° (ethanol).

Sources & evidence

ORD record
ord-ab38eb5af0614fbfb34d4b88e74bb901
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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