Acetylthioacetylchloride → (2S)-1-[2-(acetylthio)-1-oxoethyl]-4-[(2-furyl)methyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid

HRID 223737Notes

Reaction equation

[C:1]([N:11]1[CH2:18][C:17]([CH2:20][C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)(O)[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])([O:3]CC1C=CC=CC=1)=O.C(CC(Cl)=S)(=O)C.[C:33]([S:36][CH2:37]C(N1CC=C[C@@]1(CC1OC=CC=1)C(O)=O)=O)(=[O:35])[CH3:34]>>[C:33]([S:36][CH2:37][C:1]([N:11]1[CH2:18][C:17]([CH2:20][C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)=[CH:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:3])(=[O:35])[CH3:34]

Participants

Reactant 3

HCID 23301560Acetylthioacetylchloride

HCID 54161613N-carbobenzyloxy-4-[(2-furyl)methyl]-4-hydroxy-L-proline

HCID 57067544(2S)-1-[2-(Acetylthio)-1-oxoethyl]-[(2-furyl)methyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid

Product 1

HCID 57078237(2S)-1-[2-(acetylthio)-1-oxoethyl]-4-[(2-furyl)methyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid

Procedure

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

Sources & evidence

ORD record: ord-1e898a842eb54e96a8b4c5311cd43ad6
Source dataset: uspto-grants-1982_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04356182

Reaction notes

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