p-Toluenesulfonic acid monohydrate → 4-(R,S)-(t-butoxycarbonylamino)-3-oxo-1,2diazolidine p-toluenesulfonate salt

HRID 1086107Notes

Reaction equation

HRID 1086107 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][NH:12][NH:11][C:10]1=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([OH:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(Cl)Cl>[C:16]1([CH3:26])[CH:17]=[CH:18][C:19]([S:22]([OH:25])(=[O:23])=[O:24])=[CH:20][CH:21]=1.[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][NH:12][NH:11][C:10]1=[O:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 13773679TERT-BUTYL 3-OXOPYRAZOLIDIN-4-YLCARBAMATE

Product 1

HCID 200591514-(R,S)-(t-butoxycarbonylamino)-3-oxo-1,2diazolidine p-toluenesulfonate saltYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(R,S)-(t-Butoxycarbonylamino)-3-oxo-1,2-diazolidine (1.7 g, 8.45 mmol) was slurried in methylene chloride (50 ml). p-Toluenesulfonic acid hydrate (1.6 g, 8.45 mmol) was added to the slurry. After 20 minutes the resultant solid material was collected then dried in vacuo for approximately 48 hours to yield 2.95 g of colorless 4-(R,S)-(t-butoxycarbonylamino)-3-oxo-1,2-diazolidine p-toluenesulfonate salt: n.m.r. (90 MHz, DMSO-d6): δ 7.5 (d, 2, J=8), 7.1 (d, 2, J=8), 4.32 (m, 1), 3.9 (m, 1), 3.4 (m, 1) 2.3 (s, 3), 1.4 (s, 9); i.r. (KBr): 1742, 1704, 1537 cm-1.

Workup

  1. customAfter 20 minutes the resultant solid material was collected
  2. customthen dried in vacuo for approximately 48 hours

Sources & evidence

ORD record
ord-e2d9681a8af04893a06733afe3c404b4
Source dataset
uspto-grants-1991_04
Patent number
US05011938

Reaction notes

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