Ammonium → HCID 131724066, compound

HRID 1167277Notes

Reaction equation

HRID 1167277 reaction equation
[CH2:1]([C@H:8]([NH:43][C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[C@@H:9]([OH:42])[CH:10]([NH:30][S:31]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)(=[O:33])=[O:32])[CH2:11][C:12]([CH3:29])([CH3:28])[CH2:13][CH2:14][O:15][C:16]([O:18]C1C=CC([N+]([O-])=O)=CC=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+:51]>O1CCCC1.C(OCC)C>[CH2:1]([C@H:8]([NH:43][C:44](=[O:50])[O:45][C:46]([CH3:48])([CH3:47])[CH3:49])[C@@H:9]([OH:42])[CH:10]([NH:30][S:31]([C:34]1[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=1)(=[O:33])=[O:32])[CH2:11][C:12]([CH3:28])([CH3:29])[CH2:13][CH2:14][O:15][C:16](=[O:18])[NH2:51])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 223AmmoniumHCID 131724067HCID 131724067, compound

Product 1

HCID 131724066HCID 131724066, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of the product from step 1 (520 mg, 0.73 mmol) in tetrahydrofuran (10 mL) at 5° C. was added ammonium hydroxyde (30%, 2 mL) and the reaction was stirred at 5° C. for 40 minutes. The mixture was diluted with ethyl ether, washed with saturated sodium bicarbonate, dried (magnesium sulfate), and evaporated to provide the title compound (490 mg) containing p-nitrophenol (˜10%). 1H NMR (DMSO-d6): δ 0.93 (3H, s), 0.96 (3H, s), 1.2 (9H, s), 1.6 (2H, t), 2.45 (1H, dd), 2.78 (1H, d), 2.85-2.95 (2H, m), 3.3-3.6 (3H, m), 3.7 (1H, quartet), 3.8 (3H, s), 3.96 (2H, t), 5.0 (1H, d), 6.4 (2H, br s), 6.6 (1H, d), 7.05 (2H, d), 7.10-7.25 (5H, m), 7.7 (2H, d).

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialdried (magnesium sulfate)
  3. customevaporated

Sources & evidence

ORD record
ord-54b0486cc5d24da1a06f06d2a9f36c1d
Source dataset
uspto-grants-2003_09
Patent number
US06617350B2

Reaction notes

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