Ethanol → HCID 57880341, compound

HRID 1817201Notes

Reaction equation

HRID 1817201 reaction equation
C([C@@H]1COC(=O)[N:9]1[C:14]([C@@H:16]([S:28][C:29]1[CH:39]=[CH:38][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][C:30]=1[N+]([O-])=O)[CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:15])C1C=CC=CC=1.C(O)C>[Pd].C(O)(=O)C>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][CH2:18][CH2:17][C@H:16]2[C:14](=[O:15])[NH:9][C:30]3[CH:31]=[C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:38]=[CH:39][C:29]=3[S:28]2)=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 57880336HCID 57880336, compound

Product 1

HCID 57880341HCID 57880341, compoundYield 471.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Ethyl 4-{[(1S)-1-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-4-(4-methoxyphenyl)butyl]thio}-3-3-nitrobenzoate (Reference Example 22) (0.62 g, 0.11 mmol), ethanol (10 ml), acetic acid (5 ml) and 10% Pd—C (1.5 g) were mixed, and the mixture was stirred for 3 hours at room temperature under a hydrogen atmosphere. The reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by a silica gel chromatography (40 g, ethyl acetate:hexane=1:3) to obtain ethyl (2S)-2-[3-(4-methoxyphenyl)propyl]-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate (0.2 g, 98.3% e.e.), i.e., the compound described in Example 7.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by a silica gel chromatography (40 g, ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-26937b608b1a46bfb3eb0aca20e9f459
Source dataset
uspto-grants-2009_10
Patent number
US07598240B2

Reaction notes

Loading…