Carbamate → HCID 70022888, compound

HRID 1167503Notes

Reaction equation

C(N(C(C)C)CC)(C)C.[S:10]1[N:14]=[CH:13][C:12]([O:15][CH2:16][C@@H:17]2[O:21][C:20](=[O:22])[N:19]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:34][C@@H:33]5[CH2:35][C@H:30]4[CH2:31][N:32]5CC4C=CC=CC=4)=[C:25]([F:43])[CH:24]=3)[CH2:18]2)=[N:11]1.C(=O)([O-])N.C([Cl:55])C1C=CC=CC=1.CCCC(C)C>ClCCl.CO>[ClH:55].[S:10]1[N:14]=[CH:13][C:12]([O:15][CH2:16][C@@H:17]2[O:21][C:20](=[O:22])[N:19]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:34][C@@H:33]5[CH2:35][C@H:30]4[CH2:31][NH:32]5)=[C:25]([F:43])[CH:24]=3)[CH2:18]2)=[N:11]1

Participants

Conditions

Temperature: 5 °C

Procedure

Diisopropylethylamine (52 mg, 0.4 mmol) was added dropwise to a stirred solution at 5° C. under nitrogen of 5(R)-1,2,5-Thiadiazol-3-yloxymethyl-3-(4-[(1S)(4S)-2-benzyl-2,5-diazabicyclo{2,2,1}heptan-5-yl]-3-fluorophenyl)oxazolidin-2-one (0.65 g, 1.35 mmol) in dichloromethane (10 ml), followed by 1-chloroethyl chlorofornate (0.19 ml, 1.76 mmol). The mixture was stirred at 5° C. for 2 hours and the interrnediate carbamate was freed from benzyl chloride by trituration with three portions of isohexane (3×15 ml). The carbarnate was heated in refluxing MeOH (10 ml) for 1 hour. Solvent was evaporated and the residue triturated with acetone to give the title product as a solid (0.366 g, 63% yield). MS: 391 (MH+); NMR(CDCl3); 2.0 (2H, dd); 3.2-3.34 (2H+DMSO); 3.56 (2H, dd); 3.9 (1H, m); 4.18 (1H, t); 4.34 (1H, s); 4.5 (1H, s); 5.07 (1H, m); 6.86 (1H, t); 7.15 (1H, d); 7.45 (1H, d); 8.42 (1H, s); 9.04 (1H, bs); 9.57 (1H, bs).

Workup

temperatureThe carbarnate was heated
customSolvent was evaporated
customthe residue triturated with acetone

Sources & evidence

ORD record: ord-b07960795ffd49f69ae607bef4050a40
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06617339B1

Reaction notes

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