3-[[(4-Methoxy)phenylmethyl]thio]-2-methylthiopropionyl chloride → [8S]-7-[3-[[(4-Methoxy)phenylmethyl]thio]-2-methylthio-1-oxopropyl]-7-aza-1,4-dithiaspiro[4.4]-nonane-8-carboxylic acid

HRID 1106083Notes

Reaction equation

HRID 1106083 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]SCC(C)C(Cl)=S)=[CH:5][CH:4]=1.[SH:17][CH2:18][CH:19]([S:36][CH3:37])[C:20]([N:22]1[C@H:32]([C:33]([OH:35])=[O:34])[CH2:31][C:24]2(C(=O)CCC2=O)[CH2:23]1)=[O:21]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][S:17][CH2:18][CH:19]([S:36][CH3:37])[C:20]([N:22]2[C@H:32]([C:33]([OH:35])=[O:34])[CH2:31][C:24]3([S:36][CH2:19][CH2:18][S:17]3)[CH2:23]2)=[O:21])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 542258353-[[(4-Methoxy)phenylmethyl]thio]-2-methylthiopropionyl chloride2×HCID 57148383(8S)-7-(3-mercapto-2-methylthio-1-oxopropyl)-1,4-dioxo-7-azaspiro[4.4]nonane-8-carboxylic acid

Product 1

HCID 22818909[8S]-7-[3-[[(4-Methoxy)phenylmethyl]thio]-2-methylthio-1-oxopropyl]-7-aza-1,4-dithiaspiro[4.4]-nonane-8-carboxylic acid

Procedure

The 3-[[(4-methoxy)phenylmethyl]thio]-2-methylthiopropionyl chloride from part (a) is reacted with 4,4-ethylenedithio-L-proline according to the procedure of Example 9 (d) to yield [8S]-7-[3-[[(4-methoxy)phenylmethyl]thio]-2-methylthio-1-oxopropyl]-7-aza-1,4-dithiaspiro[4.4]nonane-8-carboxylic acid.

Sources & evidence

ORD record
ord-1e29d1bd29e54ae78172f163441e9d7b
Source dataset
uspto-grants-1982_01
Patent number
US04311697

Reaction notes

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