Glycine → 2-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)acetic acid

HRID 20635

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[C:7]([O:14][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[O:5][C:4](=[O:20])[CH:3]=1.[NH2:21][CH2:22][C:23]([OH:25])=[O:24].C(N(CC)CC)C>C(O)C>[CH:15]1([O:14][C:7]2[C:8]([O:12][CH3:13])=[CH:9][CH:10]=[C:11]3[C:6]=2[O:5][C:4](=[O:20])[CH:3]=[C:2]3[NH:21][CH2:22][C:23]([OH:25])=[O:24])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 4-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (170 mg, 0.58 mmol), glycine (52 mg, 0.69 mmol), triethylamine (0.2 mL, 1.4 mmol), and ethanol (2 mL) was heated at 75° C. in a sealed vial. After 2 d, more glycine (136 mg, 1.8 mmol) and triethylamine (0.3 mL, 2.2 mmol) were added. The reaction was heated at 75° C. for an additional day, allowed to cool to rt, concentrated, diluted with ethyl acetate (40 mL), and then washed with 1N HCl (50 mL×3). The organic layer was dried, filtered, and concentrated to give 2-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)acetic acid: 1H NMR (400 MHz, DMSO-d6): δ 7.87 (t, 1H), 7.68 (d, 1H), 7.08 (d, 1H), 4.88 (s, 1H), 4.81 (m, 1H), 4.00 (d, 2H), 3.87 (s, 3H), 1.90-1.44 (m, 8H); MS (ESI): 333.9.

Workup

temperatureThe reaction was heated at 75° C. for an additional day
temperatureto cool to rt
concentrationconcentrated
additiondiluted with ethyl acetate (40 mL)
washwashed with 1N HCl (50 mL×3)
customThe organic layer was dried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-e2676196ca42441280b61b4547524802
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745646B2

Linked notes

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