p-Toluenesulfonic acid → HCID 86587971, compound

HRID 1634028Notes

Reaction equation

HRID 1634028 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:3]=1[C:4]([O:6][CH2:7][C:8](=[O:26])[C@@H:9]([NH:18]C(OC(C)(C)C)=O)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5].C1(C)C=CC([S:38]([OH:41])(=[O:40])=[O:39])=CC=1>CCOCC>[C:3]1([CH3:4])[C:2]([S:38]([OH:41])(=[O:40])=[O:39])=[CH:30][CH:29]=[CH:28][CH:27]=1.[Cl:1][C:2]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:3]=1[C:4]([O:6][CH2:7][C:8](=[O:26])[C@@H:9]([NH2:18])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54433102HCID 54433102, compound

Product 1

HCID 86587971HCID 86587971, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

The crude (S)-3-tert-butoxycarbonylamino-2-oxo-5-phenylpentyl 2,5-dichlorobenzoate was dissolved in ether (5 mL) and a solution of azeotropically dried p-toluenesulfonic acid (1.31 g, 7.7 mmol) in ether (5 mL) was added. The mixture was stirred at room temperature for approximately 12 hours and then ether (200 mL) was added to provide a solid material. The solid material was broken up, filtered, washed with ether (2×50 mL) and dried in vacuo to provide (S)-3-amino-2-oxo-5-phenylpentyl 2,5-dichlorobenzoate toluenesulfonic acid salt (1.24 g, 2.3 mmol).

Workup

  1. customto provide a solid material
  2. filtrationfiltered
  3. washwashed with ether (2×50 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-62f75942172247ac8676006c6ee080c8
Source dataset
uspto-grants-2003_01
Patent number
US06506733B1

Reaction notes

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