L-Proline → HCID 86737263, compound

HRID 903469Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:18]=[CH:17][C:8]([C:9](/[C:11](/[CH3:16])=[CH:12]\[C:13]([OH:15])=O)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[NH:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([OH:23])=[O:22]>>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:9](/[C:11](/[CH3:16])=[CH:12]\[C:13]([N:19]2[CH2:26][CH2:25][CH2:24][C@H:20]2[C:21]([OH:23])=[O:22])=[O:15])=[O:10])=[CH:17][CH:18]=1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 145742L-Proline

HCID 10922858HCID 10922858, compound

Product 1

HCID 86737263HCID 86737263, compound

Procedure

As for Example 8, 3-(4-acetamidobenzoyl)crotonic acid is coupled to L-proline to give 1-[3-(4-acetamidobenzoyl)crotonyl]-L-proline. Reaction of the preceding compound with thiolacetic acid in carbontetrachloride as for Example 8 gives the product of the example as a glass.

Sources & evidence

ORD record: ord-21e6a615aec7441d86b48b2ee8e87629
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04226775

Reaction notes

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