Hydrochloric Acid → (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(ethyl)amino)acetic acid

HRID 2207067Notes

Reaction equation

HRID 2207067 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([NH:10][C@@H:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][OH:14])[C:7]([CH2:18][C:19]2[CH:34]=[CH:33][C:22]([CH2:23][N:24]([CH2:31][CH3:32])[CH2:25][C:26]([O:28]CC)=[O:27])=[CH:21][C:20]=2[O:35][CH3:36])=[C:6]([CH3:37])[N:5]=1.Cl>CO>[NH2:3][C:4]1[N:9]=[C:8]([NH:10][C@@H:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][OH:14])[C:7]([CH2:18][C:19]2[CH:34]=[CH:33][C:22]([CH2:23][N:24]([CH2:31][CH3:32])[CH2:25][C:26]([OH:28])=[O:27])=[CH:21][C:20]=2[O:35][CH3:36])=[C:6]([CH3:37])[N:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117999083(S)-ethyl 2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(ethyl)amino)acetate

Product 1

HCID 72548786(S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(ethyl)amino)acetic acidYield 102.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3M-sodium hydroxide (1 mL) was added to a solution of the product from step (viii) (310 mg) in methanol (3 mL). The solution was stirred at RT for 16 h. The reaction mixture was neutralized with 4M-hydrogen chloride (1 mL) and extracted with chloroform/EtOH (3/1). The combined organic layer was dried and concentrated under reduced pressure to afford the sub-title compound (300 mg) as a colourless amorphous solid; 1H NMR (DMSO); 7.00 (1H, s), 6.79 (1H, d), 6.72 (1H, d), 5.87 (2H, br s), 5.63 (1H, d), 4.20-4.14 (1H, m), 3.83 (3H, s), 3.76 (2H, s), 3.60 (2H, s), 3.27 (2H, q), 3.13 (2H, s), 2.66 (2H, q), 2.02 (3H, s), 1.60-1.51 (1H, m), 1.45-1.31 (3H, m), 1.13-1.06 (2H, m), 1.00 (3H, t), 0.75 (3H, t).

Workup

  1. extractionextracted with chloroform/EtOH (3/1)
  2. customThe combined organic layer was dried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1e43d31077cc47fbbc1db21c68cf0f3c
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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