Acetamide → HCID 20638830, compound

HRID 1276454Notes

Reaction equation

[C:1](N)(=O)C.[O:5]=[C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH2:18][N:19]([C:23](=[O:29])[CH2:24][O:25]C(=O)C)[CH2:20][CH2:21][CH:22]=3)=[C:13]([F:30])[CH:12]=2)[CH2:9][C@H:8]([CH2:31][NH:32][C:33](=[O:35])[CH3:34])[O:7]1>>[OH:25][CH2:24][C:23]([N:19]1[CH2:1][CH:18]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([N:10]3[CH2:9][C@H:8]([CH2:31][NH:32][C:33](=[O:35])[CH3:34])[O:7][C:6]3=[O:5])=[CH:12][C:13]=2[F:30])[CH2:22][CH2:21][CH2:20]1)=[O:29]

Participants

Reactant 2

HCID 178Acetamide

HCID 15887508HCID 15887508, compound

Product 1

HCID 20638830HCID 20638830, compound

Procedure

Following the general procedure of EXAMPLE 71, and making non-critical variations but substituting (S)-N-[[2-oxo-3-[3-fluoro-4-1-[(acetoxy)acetyl]-2,3,4,7-tetrahydro-1H-azepin-5-yl]phenyl]-5-oxazolidinyl]methyl]acetamide (EXAMPLE 75, Step 3) for (S)-(-)-N-[[2-oxo-3-[3-fluoro-4-[1-[(acetoxy)acetyl]-5,6-dihydro-2H-pyridin-3yl]phenyl]-5-oxazolidinyl]methyl]acetamide, the title compound is obtained, NMR (CDCl3, 400 MHz, mixture of rotamers) 7.41, 7.09-7.18, 6.07, 6.00, 5.87, 4.78, 4.25, 4.21, 4.05, 3.92, 3.87, 3.78, 3.67, 3.51, 2.63, 2.03 and 1.97 δ and HRMS calculated for C20H24F1N3O5 : 405.1700. Found: 405.1694.

Sources & evidence

ORD record: ord-8405a437056f4cccadf51097b785b4f9
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166056

Reaction notes

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