Lithium hydroxide, monohydrate → 2-(S)-[2-(S)-Allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester

HRID 1595142Notes

Reaction equation

HRID 1595142 reaction equation
Cl.C[O:3][C:4](=[O:36])[C@@H:5]([NH:15][C:16](=[O:35])[C@@H:17]([NH:28][C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[NH:27])[NH2:26])=[CH:21][CH:20]=1)[CH2:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].O.[OH-].[Li+]>O.C1COCC1>[C:11]([O:10][C:8](=[O:9])[CH2:7][CH2:6][C@H:5]([NH:15][C:16](=[O:35])[C@@H:17]([NH:28][C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25](=[NH:26])[NH2:27])=[CH:23][CH:24]=1)[C:4]([OH:36])=[O:3])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 686148872-(S)-[2-(S)-Allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester hydrochloride

Product 1

HCID 114429402-(S)-[2-(S)-Allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2-(S)-[2-(S)-allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester hydrochloride (3.06 g, 5.8 mmol) in 100 ml of water and 30 ml of THF was added lithium hydroxide hydrate (0.49 g, 11.6 mmol). The solution was stirred at room temperature for 12 hours, evaporated, and freeze-dried. The residue was purified by chromatography on Sephadex LH20 employing n-butanol/glacial acetic acid/water (17/1/2) as eluent. Pure fractions were combined. The solvent was evaporated, the residue was taken up in water, and the aqueous solution was freeze-dried. Yield: 2.7 g (97%). MS: m/z=477.4 (M+H)+.

Workup

  1. customevaporated
  2. customfreeze-dried
  3. customThe residue was purified by chromatography on Sephadex
  4. customThe solvent was evaporated
  5. customthe aqueous solution was freeze-dried

Sources & evidence

ORD record
ord-58ac813d6675430ba77c3bc1b1faaa7e
Source dataset
uspto-grants-2001_09
Patent number
US06287794B1

Reaction notes

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