Sodium Hydroxide → HCID 178438919, compound

HRID 2293627Notes

Reaction equation

HRID 2293627 reaction equation
[CH3:1][C:2]([C:10]1[CH:11]=[C:12]([S:16]([NH:19][C@H:20]([C:28]([N:30]2[CH2:35][CH2:34][CH:33]([CH2:36][C:37]([O:39]CC)=[O:38])[CH2:32][CH2:31]2)=[O:29])[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[NH:27])[NH2:26])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[CH3:9][C:2]([C:10]1[CH:11]=[C:12]([S:16]([NH:19][C@H:20]([C:28]([N:30]2[CH2:35][CH2:34][CH:33]([CH2:36][C:37]([OH:39])=[O:38])[CH2:32][CH2:31]2)=[O:29])[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[NH:26])[NH2:27])(=[O:17])=[O:18])[CH:13]=[CH:14][CH:15]=1)([CH3:1])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178470717HCID 178470717, compound

Product 1

HCID 178438919HCID 178438919, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 1-(Nα -(3-(α,α-dimethylbenzyl)benzenesulphonyl)-(S)-arginyl)-4-(ethoxycarbonylmethyl)piperidine (500 mg) in absolute ethanol (2.5 ml) is added aqueous 1M NaOH (1.7 ml) and the mixture is stirred for 24 hours at room temperature. The reaction mixture is then chromatographed on Amberlite resin CG120(H+) (25 ml). The resin column is eluted fast with aqueous 50% ethanol until neutral pH, then with ethanol/H2O/NH3 (sp.gr. 0.88) (5:4:1). The fractions containing the product are evaporated to give a residue which is co-evaporated (3 times) with ethanol, triturated with ether, collected by filtration, washed with ether and dried in vacuo. Thus is obtained 1-(Nα -(3-(α,α-dimethylbenzyl)benzenesulphonyl)-(S)-arginyl)piperidine-4-acetic acid, m.p. 188°-191° C., Rf (BuOH/HOAc/H2O 3:1:1) 0.58. 13C NMR spectrum is consistent with the product.

Workup

  1. customThe reaction mixture is then chromatographed on Amberlite resin CG120(H+) (25 ml)
  2. washThe resin column is eluted fast with aqueous 50% ethanol until neutral pH
  3. additionThe fractions containing the product
  4. customare evaporated
  5. customto give a residue which
  6. customtriturated with ether
  7. filtrationcollected by filtration
  8. washwashed with ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-8602c29ab68a4f4880571b3da8aa72ed
Source dataset
uspto-grants-1997_11
Patent number
US05686564

Reaction notes

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