Methyl 4-hydroxy-2,5-dimethylbenzoate → HCID 57403305, compound

HRID 1096476Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:15])([CH3:14])[C:10]([O:12]C)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:16][C:17]1[CH:25]=[C:24]([O:26][CH2:27][C@@H:28]2[CH2:33][N:32]([CH3:34])[C:31]3[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=3[O:29]2)[C:23]([CH3:39])=[CH:22][C:18]=1[C:19](Cl)=[O:20].OC1C(C)=CC(C(OC)=O)=C(C)C=1>>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]([CH3:15])([CH3:14])[C:10]([OH:12])=[O:11])=[CH:3][C:2]=1[NH:1][C:19](=[O:20])[C:18]1[CH:22]=[C:23]([CH3:39])[C:24]([O:26][CH2:27][C@@H:28]2[CH2:33][N:32]([CH3:34])[C:31]3[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=3[O:29]2)=[CH:25][C:17]=1[CH3:16]

Participants

Reactant 3

HCID 22615980Methyl 4-hydroxy-2,5-dimethylbenzoate

HCID 23125543HCID 23125543, compound

HCID 86609831HCID 86609831, compound

Product 1

HCID 57403305HCID 57403305, compoundYield 66.1%

Procedure

By the same procedures as a series of Example 18 and Example 19 using the compound (139 mg) prepared in Example 16 and 2,5-dimethyl-4-(((2S)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy)benzoylchloride (211 mg) (the compound prepared by the same procedures as a series of Example 8→Example 9→Example 10 using methyl 4-hydroxy-2,5-dimethylbenzoate.), the title compound (211 mg) having the following physical data was obtained.

Sources & evidence

ORD record: ord-3094b3de5c6a4d4ca436723eeffb83bd
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138335B2

Reaction notes

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