Acetic Anhydride → HCID 86730726, compound

HRID 633852Notes

Reaction equation

C(N(CC)CC)C.[C:8]([O:12][C:13](=[O:39])[NH:14][C@@H:15]1[CH2:20][CH2:19][C@@H:18]([CH2:21][CH:22]2[O:37][C:25]3[CH:26]=[N:27][C:28]4[CH:29]=[CH:30][C:31]([O:35][CH3:36])=[C:32]([F:34])[C:33]=4[C:24]=3[CH:23]2[OH:38])[O:17][CH2:16]1)([CH3:11])([CH3:10])[CH3:9].[C:40](OC(=O)C)(=[O:42])[CH3:41].CCCCCC>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[C:8]([O:12][C:13]([NH:14][C@H:15]1[CH2:16][O:17][CH:18]([CH2:21][C@@H:22]2[O:37][C:25]3[CH:26]=[N:27][C:28]4[CH:29]=[CH:30][C:31]([O:35][CH3:36])=[C:32]([F:34])[C:33]=4[C:24]=3[CH:23]2[O:38][C:40](=[O:42])[CH3:41])[CH2:19][CH2:20]1)=[O:39])([CH3:11])([CH3:9])[CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

4-Dimethylaminopyridine (16 mg, 0.13 mmol, 0.5 eq) and triethylamine (112 μL, 0.80 mmol, 3.0 eq) are added at 0° C. to a stirred solution of (3R,6S)-[6-(9-fluoro-1-hydroxy-8-methoxy-1,2-dihydro-furo[2,3-c]quinolin-2-ylmethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester (120 mg, 0.27 mmol, 1.0 eq) in dichloromethane (10 mL), followed by acetic anhydride (38 μL, 0.40 mmol, 1.5 eq). After 1 hour stirring at 0° C., the reaction mixture is quenched with ethanol (1 mL), solvents are evaporated to give a crude product that is purified by column chromatography (silica gel, eluent: n-hexane:ethyl acetate, 5:1 to 1:1, v/v) to afford acetic acid 2-(2S,5R)-(5-tert-butoxycarbonylamino-tetrahydro-pyran-2-ylmethyl)-9-fluoro-8-methoxy-1,2-dihydro-furo[2,3-c]quinolin-1-yl ester as a light yellow solid (89 mg, 68% yield).

Workup

customthe reaction mixture is quenched with ethanol (1 mL), solvents
customare evaporated
customto give a crude product that
customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record: ord-29d8bec8e3d748df8eea780d8e8324e5
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321788B2

Reaction notes

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