Menbutone → HCID 53786813, compound

HRID 903458Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([CH2:15][CH2:16][C:17]([OH:19])=O)=[O:14])=[CH:5][CH:4]=1.[NH:20]1[CH2:27][CH2:26][CH2:25][C@H:21]1[C:22]([OH:24])=[O:23]>>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([CH2:15][CH2:16][C:17]([N:20]2[CH2:27][CH2:26][CH2:25][C@H:21]2[C:22]([OH:24])=[O:23])=[O:19])=[O:14])=[CH:5][CH:4]=1

Participants

Reactant 2

HCID 71818Menbutone

HCID 145742L-Proline

Product 1

HCID 53786813HCID 53786813, compound

Procedure

3-(4-Methoxy-1-naphthoyl)propionic acid is coupled to L-proline as described in Examples 15 and 16 to give 1-[3-(4-methoxy-1-naphthoyl)propionyl]-L-proline. The preciding compound is reacted with bromine in acetic acid as in Example 26 and the product reacted with potassium thioacetate in ethanol to give the product of the Example as a glass.

Sources & evidence

ORD record: ord-168cccdb3ab242ac9e3f7797e24b3e40
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04226775

Reaction notes

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