p-Toluenesulfonic acid monohydrate → HCID 131720818, compound

HRID 2393233Notes

Reaction equation

HRID 2393233 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:13]C(=O)OC(C)(C)C)[CH:7]=[C:8]([C:10]([OH:12])=[O:11])[CH:9]=1)([OH:3])=[O:2].O.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([OH:31])(=[O:30])=[O:29])=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[C:22]1([CH3:32])[CH:23]=[CH:24][C:25]([S:28]([OH:31])(=[O:29])=[O:30])=[CH:26][CH:27]=1.[NH2:13][C:6]1[CH:7]=[C:8]([C:10]([O:12][CH2:1][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:11])[CH:9]=[C:4]([CH:5]=1)[C:1]([O:3][CH2:32][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 155459685-(tert-Butoxycarbonylamino)isophthalic acid

Product 1

HCID 131720818HCID 131720818, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Carbamate (7.61) (3.75 g, 8 mmol) and p-toluenesulfonic acid monohydrate (1.5 g, 8 mmol) were dissolved in toluene (55 ml) and heated at 80° C. for 45 min. A white precipitate formed during the reaction. This was collected by filtration, washed with hexanes, and dried to give the title compound which recrystallised from toluene as a white crystalline solid (needles) (3.91 g, 96%). M.p. 200°-201° C.; m/z (+ES) 362 (100%, M+H+); δH (250 MHz, d6 -DMSO) 2.5 (3H, s, CH3), 5.35 (4H, s, 2×Ar--CH2), 7.05 (2H, d, J 7.5 Hz 2×Ar--H), 7.25-7.60 (12H, m, 12×Ar--H), 7.75 (2H, d, 2×Ar--H), 8.00 (1H, s, Ar--H); δC (62.5 MHz, δ6-DMSO) 21.24, 67.08, 118.13, 121.94, 122.61, 125.95, 128.63, 128.74, 129.04, 131.52, 136.31, 138.40, 143.88, 145.65, 165.84; RF 0.15 [DCM/methanol (9:1).

Workup

  1. customA white precipitate formed during the reaction
  2. filtrationThis was collected by filtration
  3. washwashed with hexanes
  4. customdried

Sources & evidence

ORD record
ord-f4bc65ab92a741fe8023740bf8ff203c
Source dataset
uspto-grants-1998_09
Patent number
US05807688

Reaction notes

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