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

HRID 35744Notes

Reaction equation

HRID 35744 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, 8.45mmol) 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-12a4eb7658234390a101b231064c9eb0
Source dataset
uspto-grants-1988_08
Patent number
US04767871

Reaction notes

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