Lithium hydroxide, monohydrate → HCID 86271573, compound

HRID 528009Notes

Reaction equation

HRID 528009 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15]([C:17]4[CH2:18][CH2:19][N:20]([CH:23]5[CH2:28][CH2:27][CH:26]([C:29]([O:31]CC)=[O:30])[CH2:25][CH2:24]5)[CH2:21][CH:22]=4)[NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1.O.[OH-].[Li+]>O1CCCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15]([C:17]4[CH2:18][CH2:19][N:20]([CH:23]5[CH2:24][CH2:25][CH:26]([C:29]([OH:31])=[O:30])[CH2:27][CH2:28]5)[CH2:21][CH:22]=4)[NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 90418066HCID 90418066, compound

Product 1

HCID 86271573HCID 86271573, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of Example 86A (266 mg, 0.556 mmol) in 4 mL of tetrahydrofuran/water (3:1) was added lithium hydroxide mono hydrate (46.7 mg, 1.112 mmol). The reaction was stirred at room temperature overnight. The volatiles were then removed, and the residue dissolved in 5 mL water and the pH was adjusted to pH ˜6-7 with 1 M hydrochloric acid. The solid was collected by filtration and dried under high vacuum overnight to give the title compound as a hydrochloride salt. 1H NMR (400 MHz, DMSO-d6) δ 12.26 (s, 1H) 8.81 (s, 1H) 7.13-7.52 (m, 3H) 6.62 (s, 1H) 6.32 (s, 1H) 3.83 (s, 3H) 3.32 (d, J=21.06 Hz, 2H) 2.67-2.86 (m, 2H) 2.56 (s, 1H) 2.41 (s, 1H) 2.10-2.27 (m, 1H) 1.83-2.08 (m, 3H) 1.24-1.76 (m, 6H). MS (ESI+) m/z 451.1 (M+H)+.

Workup

  1. customThe volatiles were then removed
  2. dissolutionthe residue dissolved in 5 mL water
  3. filtrationThe solid was collected by filtration
  4. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-3b2331320107430cae69d2cb02af68fe
Source dataset
uspto-grants-2016_05
Patent number
US09346813B2

Reaction notes

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