Trifluoroacetic acid → [8S]-7-(3-mercapto-2-methylthio-1-oxo-propyl)-7-aza-1,4-dithiaspiro[4.4]nonane-8-carboxylic acid

HRID 1106084Notes

Reaction equation

COC1C=CC(C[S:10][CH2:11][CH:12]([S:27][CH3:28])[C:13]([N:15]2[C@H:23]([C:24]([OH:26])=[O:25])[CH2:22][C:17]3([S:21][CH2:20][CH2:19][S:18]3)[CH2:16]2)=[O:14])=CC=1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[SH:10][CH2:11][CH:12]([S:27][CH3:28])[C:13]([N:15]1[C@H:23]([C:24]([OH:26])=[O:25])[CH2:22][C:17]2([S:21][CH2:20][CH2:19][S:18]2)[CH2:16]1)=[O:14]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

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

Product 1

HCID 57153156[8S]-7-(3-mercapto-2-methylthio-1-oxo-propyl)-7-aza-1,4-dithiaspiro[4.4]nonane-8-carboxylic acid

Procedure

The product from part (b) is mixed with trifluoroacetic acid and anisole under nitrogen. The solvents are removed under vacuum to yield as a residue [8S]-7-(3-mercapto-2-methylthio-1-oxo-propyl)-7-aza-1,4-dithiaspiro[4.4]nonane-8-carboxylic acid.

Workup

customThe solvents are removed under vacuum

Sources & evidence

ORD record: ord-f73faca0ad1e425eacc32d6031b32cde
Source dataset: uspto-grants-1982_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04311697

Reaction notes

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