4-Acetylthiobutyroyl chloride → (2S)-1-[4-(acetylthio)-1-oxobutyl]-2,5-dihydro-4-[(4-methyl)phenyl]-1H-pyrrole-2-carboxylic acid

HRID 1578134Notes

Reaction equation

HRID 1578134 reaction equation
C(N1CC(O)(C2C=CC(C)=CC=2)C[C@H]1C(O)=O)(OCC1C=CC=CC=1)=O.C(CCCC(Cl)=S)(=O)C.[C:36]([S:39][CH2:40][CH2:41][CH2:42][C:43]([N:45]1[CH2:52][C:51](O)([C:53]2[CH:58]=[CH:57][C:56]([CH3:59])=[CH:55][CH:54]=2)[CH2:50][C@H:46]1[C:47]([OH:49])=[O:48])=[O:44])(=[O:38])[CH3:37]>>[C:36]([S:39][CH2:40][CH2:41][CH2:42][C:43]([N:45]1[CH2:52][C:51]([C:53]2[CH:54]=[CH:55][C:56]([CH3:59])=[CH:57][CH:58]=2)=[CH:50][C@H:46]1[C:47]([OH:49])=[O:48])=[O:44])(=[O:38])[CH3:37]

Participants

4

Reactant 3

HCID 204284874-Acetylthiobutyroyl chlorideHCID 228174921-[4-(Acetylthio)-1-oxobutyl]-4-hydroxy-4-[(4-methyl)phenyl]-L-prolineHCID 22817588N-carbobenzyloxy-4-hydroxy-4-[(4-methyl)phenyl]-L-proline

Product 1

HCID 57161405(2S)-1-[4-(acetylthio)-1-oxobutyl]-2,5-dihydro-4-[(4-methyl)phenyl]-1H-pyrrole-2-carboxylic acid

Procedure

The 3,4-dehydro-4-[(4-methyl)phenyl]-L-proline from part (a) is reacted with 4-acetylthiobutyroyl chloride according to the procedure of Example 3 (b) to yield (2S)-1-[4-(acetylthio)-1-oxobutyl]-2,5-dihydro-4-[(4-methyl)phenyl]-1H-pyrrole-2-carboxylic acid.

Sources & evidence

ORD record
ord-490ef3a585fc444da9af1c104389064c
Source dataset
uspto-grants-1981_09
Patent number
US04291040

Reaction notes

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