Propionic Acid → HCID 10287225, compound

HRID 2306618Notes

Reaction equation

HRID 2306618 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[NH2:16][CH2:17][C@@H:18]1[O:22][C:21](=[O:23])[N:20]([C:24]2[CH:29]=[CH:28][C:27]([C:30]3[S:31][CH2:32][C:33](=[O:36])[NH:34][N:35]=3)=[C:26]([F:37])[CH:25]=2)[CH2:19]1.C(N(CC)C(C)C)(C)C.[C:47](O)(=[O:50])[CH2:48][CH3:49]>CN(C=O)C>[F:37][C:26]1[CH:25]=[C:24]([N:20]2[CH2:19][C@H:18]([CH2:17][NH:16][C:47](=[O:50])[CH2:48][CH3:49])[O:22][C:21]2=[O:23])[CH:29]=[CH:28][C:27]=1[C:30]1[S:31][CH2:32][C:33](=[O:36])[NH:34][N:35]=1

Participants

6

Reactant 4

HCID 1032Propionic AcidHCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 23528997HCID 23528997, compound

Product 1

HCID 10287225HCID 10287225, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,3-Dicyclohexylcarbodiimide (0.153 g, 0.740 mmol) is added to a mixture of 2-[4-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluorophenyl]-4H-[1,3,4]thiadiazin-5-one (0.200 g, 0.617 mmol), N,N-diisopropylethylamine (0.161 ml, 0.927 mmol) and propionic acid (0.051 ml, 0.680 mmol) in DMF (3 ml). The mixture is stirred overnight at room temperature and then partially evaporated under vacuum. The residue is diluted with water (5 ml) and the resulting precipitate is filtered and dried under vacuum. Purification by PTLC (10% MeOH/DCM) gives pure product as a white solid (0.21 g, 90%); 1HNMR (300 MHz, DMSO-d6) δ 0.94 (t, J=7.7 Hz, 3H), 2.08 (q, J=7.7 Hz, 2H), 3.40-3.48 (m, 2H), 3.59 (s, 2H), 3.77 (dd, J=6.0, 9.1 Hz, 1H), 4.14 (t, J=9.1 Hz, 1H), 4.74-4.78 (m, 1H), 7.41 (dd, J=2.2, 8.8 Hz, 1H), 7.52 (dd, J=2.2, 14 Hz, 1H), 7.69 (t, J=8.5 Hz, 1H), 8.16 (t, J=5.8 Hz, 1H), 11.6 (s, 1H); mp 192-3; MS (m/z): [M+H]+=381.

Workup

  1. custompartially evaporated under vacuum
  2. additionThe residue is diluted with water (5 ml)
  3. filtrationthe resulting precipitate is filtered
  4. customdried under vacuum
  5. customPurification by PTLC (10% MeOH/DCM)

Sources & evidence

ORD record
ord-cf7dc77f65834f0d829ea2bd6a782793
Source dataset
uspto-grants-2004_12
Patent number
US06828317B2

Reaction notes

Loading…