Ammonia → (8S)-7-(3-mercapto-2-methylthio-1-oxopropyl)-1,4-dioxo-7-azaspiro[4.4]nonane-8-carboxylic acid

Reaction equation

C([S:4][CH2:5][CH:6]([S:23][CH3:24])[C:7]([N:9]1[C@H:19]([C:20]([OH:22])=[O:21])[CH2:18][C:11]2([C:15](=[O:16])[CH2:14][CH2:13][C:12]2=[O:17])[CH2:10]1)=[O:8])(=O)C.N>>[SH:4][CH2:5][CH:6]([S:23][CH3:24])[C:7]([N:9]1[C@H:19]([C:20]([OH:22])=[O:21])[CH2:18][C:11]2([C:15](=[O:16])[CH2:14][CH2:13][C:12]2=[O:17])[CH2:10]1)=[O:8]

Participants

Reactant 2

HCID 222Ammonia

HCID 56977003(8S)-7-[3-(Acetylthio)-2-methylthio-1-oxopropyl]-1,4-dioxo-7-azaspiro[4.4]nonane-8-carboxylic acid

Product 1

HCID 57148383(8S)-7-(3-mercapto-2-methylthio-1-oxopropyl)-1,4-dioxo-7-azaspiro[4.4]nonane-8-carboxylic acid

Procedure

The product from part (c) is treated with concentrated ammonia according to the procedure of Example 2 to yield (8S)-7-(3-mercapto-2-methylthio-1-oxopropyl)-1,4-dioxo-7-azaspiro[4.4]nonane-8-carboxylic acid.

Sources & evidence

ORD record: ord-3b397fe47e5f420eb7f734036e2217ea
Source dataset: uspto-grants-1982_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04311697

Reaction notes

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