Acetic Anhydride → ethyl 2-(N-(4-((2-amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)acetamido)acetate

HRID 2207078Notes

Reaction equation

HRID 2207078 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[N:14]=[C:13]([O:15][S:16]([C:19]2[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=2[CH3:27])(=[O:18])=[O:17])[C:12]([CH2:28][C:29]2[CH:42]=[CH:41][C:32]([CH2:33][NH:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:31][C:30]=2[O:43][CH3:44])=[C:11]([CH3:45])[N:10]=1.C(N(CC)CC)C>C1COCC1>[NH2:8][C:9]1[N:14]=[C:13]([O:15][S:16]([C:19]2[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=2[CH3:27])(=[O:18])=[O:17])[C:12]([CH2:28][C:29]2[CH:42]=[CH:41][C:32]([CH2:33][N:34]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:1](=[O:3])[CH3:2])=[CH:31][C:30]=2[O:43][CH3:44])=[C:11]([CH3:45])[N:10]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 89907264Ethyl 2-(4-((2-amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzylamino)acetate

Product 1

HCID 117992603ethyl 2-(N-(4-((2-amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)acetamido)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic anhydride (6 μL) was added to a solution of the product from step (i) (23 mg) and triethyl amine (9 μL) in THF (1 mL), and the mixture was stirred at RT for 3 h. The mixture was quenched with water, extracted with EtOAc, combined organic layer was washed with brine, dried and concentrated under reduced pressure. The sub-title compound (25 mg) was obtained as a colourless gum, which was used for next reaction without further purification; LC-MS: m/z=585.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washwas washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b303ea83d7fb47a697eb33cc34ea6e42
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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