Acetic Acid → HCID 69857170, compound

HRID 2268115Notes

Reaction equation

HRID 2268115 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]([NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH:23]=O)[CH:17]=2)=[C:10]([Cl:25])[CH:9]=1)=[O:6])[CH3:2].[NH2:27][CH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C>[CH2:1]([O:3][C:4](=[O:26])[C:5]([NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH2:23][NH:27][CH:28]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH2:30][CH2:29]3)[CH:17]=2)=[C:10]([Cl:25])[CH:9]=1)=[O:6])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 123445(+-)-1-AminoindanHCID 5049666Sodium triacetoxyborohydrideHCID 53936184HCID 53936184, compound

Product 1

HCID 69857170HCID 69857170, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a mixture of N-[3,5-dichloro-4-(3-formyl-4-hydroxy-phenoxy)-phenyl]-oxamic acid ethyl ester (30 mg, 0.08 mmol) and aminoindan (10 mg, 0.08 mmol) in dichloroethane (1.0 mL) was added sodium triacetoxyborohydride (22.4 mg, 0.11 mmol) and acetic acid (4.5 mg, 0.08 mmol) in single portions. After stirring at RT for 3 h, the solution became clear and yellow. The solution was quenched with saturated aqueous NaHCO3 (5 mL) and extracted with Et2O (3×10 mL). The combined extracts were dried over Na2SO4, filtered and concentrated to give the crude product as a yellow glass. The crude product was purified by preparative TLC (5% Et2O in CH2Cl2) to afford the title compound as an off-white solid. NMR (400 MHz, CDCl3) d 8.94 (s, 1H), 7.74 (s, 2H), 7.36-7.37 (d, 1H), 7.19-7.25 (m, 4H), 6.75-6.77 (d, 1H), 6.61-6.64 (dd, 1H), 6.54-6.55 (d, 1H), 4.40-4.46 (q, 2H), 4,30-4.33 (t, 1H), 4.05-4.08 (d, 1H), 3.95-3.98 (d, 1H), 2.98-3.06 (m, 1H), 2.81-2.88 (m, 1H), 2.42-2.51 (m, 1H), 1.88-1.96 (m, 1H), 1.41-1.45 (t, 3H). MS Calc.: 514.20, Found: 513.1 (M−1).

Workup

  1. customThe solution was quenched with saturated aqueous NaHCO3 (5 mL)
  2. extractionextracted with Et2O (3×10 mL)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product as a yellow glass
  7. customThe crude product was purified by preparative TLC (5% Et2O in CH2Cl2)

Sources & evidence

ORD record
ord-b7ca401d772c44918d4381848b360303
Source dataset
uspto-grants-2001_12
Patent number
US06326398B1

Reaction notes

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