Sodium o-formylbenzenesulfonate → (1r,5r,6s)-2-{[3-Ethoxycarbonyl-5-(1-ethyl-propoxy)-6-hydroxy-cyclohex-3-enylimino]-methyl}-benzenesulfonic acid sodium salt

HRID 495686Notes

Reaction equation

HRID 495686 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:11][C@@H:10]([NH2:12])[C@H:9]([OH:13])[C@H:8]([O:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH:7]=1)=[O:5])[CH3:2].[Na+:20].[CH:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29]([O-:32])(=[O:31])=[O:30])=O>C(O)C>[Na+:20].[CH2:1]([O:3][C:4]([C:6]1[CH2:11][C@@H:10]([N:12]=[CH:21][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29]([O-:32])(=[O:31])=[O:30])[C@H:9]([OH:13])[C@H:8]([O:14][CH:15]([CH2:16][CH3:17])[CH2:18][CH3:19])[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 3794540Sodium o-formylbenzenesulfonateHCID 10802068(3R,4S,5R)-ethyl 5-amino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Product 1

HCID 87986406(1r,5r,6s)-2-{[3-Ethoxycarbonyl-5-(1-ethyl-propoxy)-6-hydroxy-cyclohex-3-enylimino]-methyl}-benzenesulfonic acid sodium saltYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of 27.1 g (100 mmol) (3R,4S,5R)-5-amino-3-(1-ethylpropoxy)-4-hydroxycyclohexene-1-carboxylic acid ethyl ester and 20.8 g (100 mmol) 2-formylbenzenesulfonic acid sodium salt in 270 ml ethanol was heated to reflux under argon for 2 hours. The brown, turbid reaction mixture was evaporated in a rotary evaporator and the residue was treated twice with 135 ml of ethyl acetate and evaporated in a rotary evaporator at 50° C. to dryness to yield 45.88 g (99%) of (1R,5R,6S)-2-{[3-ethoxycarbonyl-5-(1-ethyl-propoxy)-6-hydroxy-cyclohex-3-enylimino]-methyl}-benzenesulfonic acid sodium salt as a yellow amorphous solid. IR (film): 3417,2924, 2726, 1714, 1638, 1464, 1378, 1237, 1091, 970 cm−1; MS (ISP-MS):438.3 (M+−Na) m/z.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under argon for 2 hours
  3. customThe brown, turbid reaction mixture
  4. customwas evaporated in a rotary evaporator
  5. additionthe residue was treated twice with 135 ml of ethyl acetate
  6. customevaporated in a rotary evaporator at 50° C. to dryness

Sources & evidence

ORD record
ord-b2392387f09949e98b177f83f9bf366c
Source dataset
uspto-grants-2005_09
Patent number
US06939986B2

Reaction notes

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