Methylamine → HCID 10287278, compound

HRID 896145Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:18]2[CH2:22][C@H:21]([C:23]([NH2:25])=[O:24])[O:20][C:19]2=[O:26])[CH:5]=[C:6]([F:17])[C:7]=1[C:8]1([CH3:16])[CH2:11][N:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:9]1.[CH3:27]N>CO>[CH3:27][NH:25][C:23]([C@@H:21]1[O:20][C:19](=[O:26])[N:18]([C:4]2[CH:3]=[C:2]([F:1])[C:7]([C:8]3([CH3:16])[CH2:9][N:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:11]3)=[C:6]([F:17])[CH:5]=2)[CH2:22]1)=[O:24]

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of methyl (5R)-3-[3,5-difluoro-4-(1-methoxycarbonyl-3-methylazetidin-3-yl]-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 57, Step 4, 500 mg, 1.30 mmol) in MeOH (10 mL) is heated at 50° C. to achieve full dissolution, then cooled to 0° C. and treated with methylamine (15 mL, 2.0 M in MeOH). The reaction mixture is stirred for 20 min at 0° C. and then concentrated under reduced pressure. Trituration (Et2O) affords the title compound as a white solid in 90% yield; 1H NMR (400 MHz, DMSO-d6) δ 8.41 (d, 1 H), 7.35 (d, 2 H), 5.09 (dd, 1 H), 4.26 (m, 2 H), 4.25 (t, 1 H), 4.02 (dd, 1 H), 3.86 (d, 2 H), 3.56 (s, 3 H), 2.66 (d, 3 H), 1.56 (s, 3H); hMS (ESI) calcd for C17H19F2N3O5+H1 384.1371, found 384.1360; [α]25D=−35 (c 0.90, DMSO).

Workup

dissolutiondissolution
temperaturecooled to 0° C.
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-bfae58fd8eae485f97140e3839b66e8f
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919329B2

Reaction notes

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