2-Aminophenol → HCID 89792702, compound

HRID 520771Notes

Reaction equation

HRID 520771 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[NH:9]([C:18](OC(C)(C)C)=O)[C@H:10]([C:15]([OH:17])=O)[C:11]([CH3:14])([CH3:13])[CH3:12]>>[C:11]([C:2]1[C:3]([OH:8])=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:18][NH:9][C@@H:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[C:15]([N:9]([CH3:18])[CH3:10])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 58012-AminophenolHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid

Product 1

HCID 89792702HCID 89792702, compound

Procedure

The title compound is prepared according to the representative synthesis of aminophenol 2g except for the following changes: 1) Initial amide formation carried out with Boc-Tle-OH instead of Boc-Val-OH. 2) The product from the reduction process is quenched with a saturated solution of aqueous NaHCO3 (formation of the HCl salt is omitted) and the desired product is purified by silica gel chromatography (9:1 hexanes:ethyl acetate to 6:1 hexanes:ethyl acetate to 4:1 hexanes:ethyl acetate) to afford 2h as a white solid. M.p.=96-98° C. IR (neat): 2948 (w, br), 1639 (s), 1460 (m), 1433 (m), 1352 (m), 1240 (m), 1135 (m), 878 (m), 782 (m), 751 (s) cm−1; 1H NMR (400 MHz, CDCl3): δ 10.87 (1H, br s), 7.19 (1H, d, J=7.3 Hz), 6.77 (1H, d, J=7.3 Hz), 6.70 (1H, t, J=7.5), 4.09 and 3.40 (2H, ABq, JAB=13.6 Hz), 3.31 (1H, d, J=11.3 Hz), 3.03 (3H, s), 2.89 (3H, s), 2.71 (1H, br s), 1.40 (9H, s), 0.96 (9H, s); 13C NMR (100 MHz, CDCl3): δ 173.3, 157.0, 137.2, 126.9, 126.3, 122.9, 118.5, 62.4, 51.3, 38.0, 35.8, 34.8, 34.7, 29.6, 27.0; HRMS Calcd for C19H33N2O2 [M+H]+: 321.25420. Found: 321.25442. [α]20D=−33 (c=0.93, CHCl3).

Workup

  1. customThe title compound is prepared
  2. custom2) The product from the reduction process is quenched with a saturated solution of aqueous NaHCO3 (formation of the HCl salt
  3. customis purified by silica gel chromatography (9:1 hexanes:ethyl acetate to 6:1 hexanes:ethyl acetate to 4:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-432cfdf245a54e1994c3edb6e8ce15b0
Source dataset
uspto-grants-2016_05
Patent number
US09328061B2

Reaction notes

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