L-Alanine → HCID 68428367, compound

HRID 642285Notes

Reaction equation

C(O[C:4]([C:6]1[N:11]=[C:10]([CH3:12])[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:22])=[O:5])C.[NH2:23][C@H:24]([C:26]([OH:28])=[O:27])[CH3:25]>C[O-].[Na+].CO>[OH:22][C:7]1[C:8]2[S:15][C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:13][C:9]=2[C:10]([CH3:12])=[N:11][C:6]=1[C:4]([NH:23][CH:24]([CH3:25])[C:26]([OH:28])=[O:27])=[O:5]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 7-hydroxy-4-methyl-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (50 mg, 0.16 mmol) and L-alanine (146 mg, 1.63 mmol) in 0.5 M sodium methoxide/methanol (2.6 mL) was heated at 120° C. in a microwave vessel for 3 h before it was cooled to room temperature and concentrated in vacuo. Water was added to the residue and extracted four times with dichloromethane until no UV spot in the dichloromethane layer. The remaining aqueous layer was acidified to pH=3 with 1N HCl (2 mL). The suspension was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo to give the title compound as a white solid (22 mg): 1H NMR (DMSO-d6, 200 MHz): δ=12.98 (br s, 1H), 9.06 (d, J=7.4 Hz, 1H), 8.15 (m, 2H), 7.61 (m, 3H), 4.54 (m, 1H), 2.88 (s, 3H), 1.49 (d, J=7.4 Hz, 3H); MS: (+) m/z 358.04 (M+1).

Workup

temperaturewas cooled to room temperature
concentrationconcentrated in vacuo
additionWater was added to the residue
extractionextracted four times with dichloromethane until no UV spot in the dichloromethane layer
extractionThe suspension was extracted with ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-17aeb23ba8774985a75257876539bcb1
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696223B2

Reaction notes

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