Lithium Hydroxide → 4-({Acetyl[(1-methyl-1H-1,2,3-triazol-4-yl)methyl]amino}methyl)benzoic acid

HRID 1942822ノート

反応式

HRID 1942822 の反応式
[C:1]([N:4]([CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=1)[CH2:5][C:6]1[N:7]=[N:8][N:9]([CH2:11][Si](C)(C)C)[CH:10]=1)(=[O:3])[CH3:2].C1COCC1.[Li+].[OH-]>CO>[C:1]([N:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=1)[CH2:5][C:6]1[N:7]=[N:8][N:9]([CH3:11])[CH:10]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59627274Methyl 4-{[acetyl({1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)amino]methyl}benzoate

生成物 1

HCID 596272824-({Acetyl[(1-methyl-1H-1,2,3-triazol-4-yl)methyl]amino}methyl)benzoic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of methyl 4-{[acetyl({1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)amino]methyl}benzoate (101 mg, 0.270 mmol), THF (809 uL) and MeOH (270 uL) was treated with aqueous LiOH (270 uL, 0.809 mmol, 3M in water). The reaction immediately turned red and was stirred overnight. The reaction was quenched with 2M aq. HCl and extracted with EtOAc 2×. The combined organic layers were washed with brine, dried (MgSO4) and concentrated to afford the protosilylated carboxylic acid as a yellow oil. MS: cal'd 361 (MH+), exp 361 (MH+).

後処理

  1. customThe reaction immediately turned red
  2. customThe reaction was quenched with 2M aq. HCl
  3. extractionextracted with EtOAc 2×
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-725f0b4eb416433d9b7c3d556a0d6e02
出典データセット
uspto-grants-2013_03
特許番号
US08389553B2

反応ノート

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