Methanol → Ammonium Hydroxide

HRID 1019320Notes

Reaction equation

HRID 1019320 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:20])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH2:19])[CH:7]([CH2:21][N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:6]1)=[O:4].C(N(CC)CC)C.CS(Cl)(=O)=O.CO>C(Cl)Cl>[NH4+:5].[OH-:2].[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:20])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH2:19])[CH:7]([CH2:21][N:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)[CH2:6]1)=[O:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22285899HCID 22285899, compound

Product 2

HCID 14923Ammonium HydroxideYield 28%HCID 22285899HCID 22285899, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Then, to a solution of the above compound d (0.15 g, 0.33 mmoL) and triethylamine (0.10 mL, 0.66 mmoL) in CH2Cl2 (10.0 mL) at 0° C. was added methanesulfonyl chloride (0.026 mL, 0.33 mmoL). The reaction was stirred for 16 hr. The reaction was diluted with CH2Cl2 (20.0 mL), washed with saturated NaHCO3 solution and water. Then, dried over Mg2SO4. Then, isolated on a silica gel column (solvent system: CH2Cl2: CH3OH: 28% NH4OH (98:2:2) to give the desired product as a free base (0.1 g, 68%). Evaporate the solvent and generate an HCl salt (0.06 gm; m.p. 130-135° C.). 1H NMR (free base 200 MHz, CDCl3) δ 1.75 (4H, m), 2.2 (1H, m), 2.5-3.1 (6H, m), 3.01 (3H, s), 3.50 (2H, m), 3.73 (3H, s), 3.8-4.5 (5H, m), 5.02 (1H, m), 6.88-7.55 (3H, Ar). MS (FAB) m/z 439. Anal. Calc. For C20H30N4O5S2.HCl: C, 50.57; H, 6.58; N, 11.79. Found: C, 50.55; H, 6.64; N, 11.36.

Workup

  1. washwashed with saturated NaHCO3 solution and water
  2. dry with materialThen, dried over Mg2SO4
  3. customThen, isolated on a silica gel column (solvent system

Sources & evidence

ORD record
ord-76eb7ef2ee6948d88d706c01676557e8
Source dataset
uspto-grants-2002_11
Patent number
US06486165B2

Reaction notes

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