Salicylic Acid → HCID 117902828, compound

HRID 520770Notes

Reaction equation

HRID 520770 reaction equation
[CH2:1]([NH:5][C:6](=[O:20])[C@@H:7]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])[CH:8]([CH3:10])[CH3:9])[CH2:2][CH2:3][CH3:4].N[C@H](C(NCCCC)=[O:27])C(C)C.C(O)(=O)C1C(=CC=CC=1)O>>[CH2:1]([NH:5][C:6](=[O:20])[C@@H:7]([NH:11][C:12](=[O:27])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])[CH:8]([CH3:9])[CH3:10])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 338Salicylic AcidHCID 11126743HCID 11126743, compoundHCID 117903039HCID 117903039, compound

Product 1

HCID 117902828HCID 117902828, compound

Procedure

The title compound is prepared according to the representative synthesis of aminophenol 2a except after the second step; H2N-Val-NHn-Bu is treated with salicylic acid under the standard amide formation conditions outlined in the first step. The resulting off-white solid is purified by silica gel chromatography (5:1 hexanes:ethyl acetate) to afford 2c as a white solid. M.p.=123-125° C. IR (neat): 3279 (w), 3090 (w, br), 2930 (m), 1620 (s), 1605 (s), 1547 (s), 1530 (s), 1454 (s), 1371 (m, br), 1229 (m), 756 (s), 643 (m) cm−1; 1H NMR (400 MHz, CDCl3): δ 12.07 (1H, s), 7.51 (1H, d, J=8.0 Hz), 7.40-7.36 (1H, m), 7.29 (1H, br s), 6.97 (1H, dd, J=8.4, 0.9 Hz), 6.85-6.81 (1H, m), 6.00 (1H, br s), 4.36 (1H, t, J=7.7 Hz), 3.39-3.30 (1H, m), 3.27-3.19 (1H, m), 2.25-2.17 (1H, m), 1.54-1.47 (2H, m), 1.39-1.30 (2H, m), 1.03 (3H, d, J=3.3 Hz), 1.01 (3H, d, J=3.2 Hz), 0.91 (3H, t, J=7.3 Hz); 13C NMR (100 MHz, CDCl3): δ 170.8, 169.8, 161.4, 134.5, 126.3, 119.0, 118.5, 114.4, 58.9, 39.6, 31.7, 31.6, 20.2, 19.3, 18.7, 13.8; HRMS Calcd for C16H25N2O3[M+H]+: 293.18652. Found: 293.18532. [α]20D=−34 (c=0.63, CHCl3).

Workup

  1. customThe title compound is prepared
  2. customThe resulting off-white solid is purified by silica gel chromatography (5:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-6394b366dfa5449cb7a04abd6f97fb81
Source dataset
uspto-grants-2016_05
Patent number
US09328061B2

Reaction notes

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