(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one → HCID 178446066, compound

HRID 1737112Notes

Reaction equation

C[CH:2]([C@H:4]1[CH2:8][O:7]C(=O)[N:5]1[C:10](=[O:37])[CH2:11][CH2:12][C:13]1[N:14]=[CH:15][N:16](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=1)[CH3:3].[CH3:38][N:39]([CH3:52])[C:40](=[O:51])[CH2:41][NH:42][C@H:43]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH3:44].[CH3:53][CH:54]([C@H:56]1[CH2:60][O:59]C(=O)N1)[CH3:55]>>[CH3:52][N:39]([CH3:38])[C:40](=[O:51])[CH2:41][N:42]([C@H:43]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH3:44])[C:8](=[O:7])[CH2:4][C@@H:11]([CH2:12][C:13]1[N:14]=[CH:15][NH:16][CH:17]=1)[C:10]([NH:5][C@@H:4]([CH2:2][CH:3]1[CH2:17][CH2:13][CH2:12][CH2:11][CH2:10]1)[C@@H:8]([OH:7])[C@@H:60]([OH:59])[CH2:56][CH:54]([CH3:53])[CH3:55])=[O:37]

Participants

Reactant 3

HCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one

HCID 28564749HCID 28564749, compound

HCID 53738541HCID 53738541, compound

Product 1

HCID 178446066HCID 178446066, compound

Procedure

4(S)-(1-Methylethyl)-3-{1-oxo-3-[1-(triphenylmethyl)-1H-imidazol-4-yl]propyl}-2-oxazolidinone: By following the procedure of example 2, section (b) and using the product of section (a) of this example (11.5 g, 30.1 mmol) to prepare the corresponding mixed anhydride which in turn is reacted with the (S)-4-(1-methylethyl)-2-oxazolidinone (3.53 g, 27.3 mmol), the desired product was obtained as a pale yellow solid (11.38 g, 84%); 1H NMR(CDCl3) δ7.36-7.29 (m,10H), 7.17-7.10 (m,6H), 6.58 (d, J=0.7 Hz,1H), 4.40 (td, J=3.8 Hz, 7.5 Hz,1H), 4.29-4.14 (m,2H), 3.32-3.23 (m,2H), 2.96-2.88 (m,2H), 2.33 (hept d, J=3.8 Hz, 6.9 Hz, 1H), 0.89 (d, J=7.0 Hz, 3H), 0.82 (d, J=6.9 Hz,3H).

Workup

customto prepare the

Sources & evidence

ORD record: ord-b8ab150ad8b04ca7bc6c6767972aed12
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05541163

Reaction notes

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