Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl ester → 1,1-Dimethylethyl (1-{(2R)-2-hydroxy-3-[7-(methyloxy)-2-oxo-3,4-dihydro-1,8-naphthyridin-1(2H)-yl]propyl}-4-piperidinyl)carbamate

HRID 1943168Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:17])[N:10]2[CH2:13][C@H:14]2[CH2:16][O:15]2)=[CH:5][CH:4]=1.[N+](C1C=C(S(OC[C@H]2CO2)(=O)=O)C=CC=1)([O-])=O.[NH:35]1[CH2:40][CH2:39][CH:38]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:37][CH2:36]1>CN(C=O)C>[OH:15][C@@H:14]([CH2:13][N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:12]=2)[CH2:7][CH2:8][C:9]1=[O:17])[CH2:16][N:35]1[CH2:36][CH2:37][CH:38]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:46])([CH3:45])[CH3:47])[CH2:39][CH2:40]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 7-(methyloxy)-1-[(2S)-2-oxiranylmethyl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one (made according to the general method of Example 5(f) but using (2R)-2-oxiranylmethyl 3-nitrobenzenesulfonate) (3.1 g, 13.3 mmol) and 1,1-dimethylethyl 4-piperidinylcarbamate (2.7 g, 13.3 mmol) in DMF (3 ml) was heated at 110° C. for 1 h. DMF was then evaporated. The crude product was purified by silica chromatography using a 0-10% methanol/dichlormethane gradient to provide the desired compound as a pale yellow solid, presumed R enantiomer (3.9 g; 89%; 90% purity).

Workup

customDMF was then evaporated
customThe crude product was purified by silica chromatography

Sources & evidence

ORD record: ord-0dcdd50330af424d95c4b33947464d91
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389524B2

Reaction notes

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