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

HRID 1761683Notes

Reaction equation

HRID 1761683 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-2b48389aedaf45369a0a7e64bb96afc1
Source dataset
uspto-grants-1989_05
Patent number
US04826993

Reaction notes

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