Methanol → HCID 20725656, compound

HRID 1582371Notes

Reaction equation

HRID 1582371 reaction equation
CC1(C)[O:6][C@H:5]([C:7]([N:9]2[CH2:14][CH2:13][C:12]([C:15]3[C:20]([F:21])=[CH:19][C:18]([N:22]4[CH2:26][C@H:25]([CH2:27][N:28]([C:36]5[S:40][N:39]=[C:38]([CH3:41])[CH:37]=5)C(OC(C)(C)C)=O)[O:24][C:23]4=[O:42])=[CH:17][C:16]=3[F:43])=[CH:11][CH2:10]2)=[O:8])[CH2:4][O:3]1.CO>ClCCl>[OH:6][C@@H:5]([CH2:4][OH:3])[C:7]([N:9]1[CH2:14][CH2:13][C:12]([C:15]2[C:20]([F:21])=[CH:19][C:18]([N:22]3[CH2:26][C@H:25]([CH2:27][NH:28][C:36]4[S:40][N:39]=[C:38]([CH3:41])[CH:37]=4)[O:24][C:23]3=[O:42])=[CH:17][C:16]=2[F:43])=[CH:11][CH2:10]1)=[O:8]

Participants

4

Reactant 2

HCID 887MethanolHCID 69584855HCID 69584855, compound

Product 1

HCID 20725656HCID 20725656, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using essentially the technique of Example 20, but starting from 3-(4-(1-(2,2-dimethyl-1,3-dioxolan-4-(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-(N-(t-butoxycarbonyl)-3-methylisothiazol-5-ylaminomethyl)oxazolidin-2-one (250 mg, 0.39 mM), and using a gradient increasing in polarity from 0 to 20% methanol in dichloromethane for chromatography, gave the desired product (92 mg). NMR (DMSO-d6) δ: 2.16 (s, 3H); 2.29 (m, 1H); 2.37 (m, 1H); 3.42 (t, 2H); 3.47 (m, 1H); 3.55 (m, 1H); 3.73 (m, 1H); 3.76 (dd, 1H); 4.10 (m, 2H); 4.14 (t, 1H); 4.24 (m, 1H); 4.36 (t, 1H); 4.68 (t, 1H); 4.87 (m, 1H); 4.97 (m, 1H); 5.86 (s, 1H); 6.97 (s, 1H); 7.31 (d, 2H); 7.38 (t, 1H). MS (ESP): 495 (MH+) for C22H24F2N4O5S

Sources & evidence

ORD record
ord-8421b1f88f5849fcb797aba74e45e866
Source dataset
uspto-grants-2004_05
Patent number
US06734200B1

Reaction notes

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