p-Toluenesulfonic acid → HCID 86758783, compound

HRID 1634031Notes

Reaction equation

HRID 1634031 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[N+:12]([CH2:15][C:16](=[O:34])[C@@H:17]([NH:26]C(=O)OC(C)(C)C)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([O-:14])=[O:13]>C(OCC)C.ClCCl>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([OH:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[NH2:26][C@@H:17]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:16](=[O:34])[CH2:15][N+:12]([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54225915HCID 54225915, compound

Product 1

HCID 86758783HCID 86758783, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution comprised of anhydrous p-toluenesulfonic acid (26 mmol) in ethyl ether (10 mL) was added to a suspension comprised of tert-butyl (S)-3-nitro-2-oxo-1-phenethylpropylcarbamate (4.5 g, 14 mmol) in dichloromethane (20 mL) and ethyl ether (150 mL). The mixture was stirred for 70 hours at room temperature and the filtered. The solid collected was washed thoroughly with ethyl ether and dried in vacuo to provide (S)-3-amino-1-nitro-5-phenylpentan-2-one p-toluenesulfonic acid salt (5.4 g, 13.7 mmol) as a white solid. 1H NMR (270 MHz, DMSO-d6): δ 1.92-2.05 (m, 1H), δ 2.15-2.28 (m, 1H), δ 2.29 (s, 3H), δ 2.56-2.76 (m, 2H), δ 4.44 (br.s, 1H), δ 6.97 (d, J=16.1 Hz, 1H), δ 6.29 (d J=16.1 Hz, 1H), δ 7.12 (d, J=8.4 Hz, 2H), δ 7.20-7.35 (m, 5H), δ 7.49 (d, J=8.2 Hz, 1H), δ 8.46 (br.s, 3 NH).

Workup

  1. additionwas added to a suspension
  2. customThe solid collected
  3. washwas washed thoroughly with ethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7733ecd4843a4b9eb716f4de2d4e6746
Source dataset
uspto-grants-2003_01
Patent number
US06506733B1

Reaction notes

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