Potassium Hydroxide → (1R,3S,5S)-5-(Tetrahydro-pyran-2-yloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester

HRID 1527431ノート

反応式

HRID 1527431 の反応式
C([O:3][C:4]([C@@H:6]1[CH2:11][C@:10]2([CH2:12][O:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][O:15]3)[C@@H:8]([CH2:9]2)[N:7]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:5])C.[OH-].[K+]>CO.C1COCC1.O.CCOC(C)=O>[C:23]([O:22][C:20]([N:7]1[C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][C@:10]2([CH2:12][O:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][O:15]3)[C@H:8]1[CH2:9]2)=[O:21])([CH3:26])([CH3:24])[CH3:25]

参加物

7

反応物 2

HCID 14797Potassium HydroxideHCID 68284099(1R,3S,5S)-5-(Tetrahydro-pyran-2-yloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester

生成物 1

HCID 68284002(1R,3S,5S)-5-(Tetrahydro-pyran-2-yloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a solution of (1R,3S,5S)-5-(tetrahydro-pyran-2-yloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester (510 mg, 1.38 mmol) in MeOH (2.3 mL), THF (2.3 mL) and water (2.3 mL) was added KOH (155 mg, 2.76 mmol). The reaction was stirred at 60° C. for 45 min. Then allowed to cool to RT and diluted with EtOAc. The layers were separated, the aqueous layer was acidified by addition of HCl (0.1N, until pH 1) and extracted with EtOAc (×2). The organics were dried (Na2SO4), filtered and concentrated. MS (UPLC/MS): 359.4 [M+NH4]+, 340.4 [M−H]−, 386.4 [M+HCOO]−, 681.5 [2M−H]−; tR (HPLC conditions f): 1.84 min.

後処理

  1. temperatureto cool to RT
  2. customThe layers were separated
  3. additionthe aqueous layer was acidified by addition of HCl (0.1N, until pH 1)
  4. extractionextracted with EtOAc (×2)
  5. dry with materialThe organics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custom1.84 min.

出典と根拠

ORDレコード
ord-b689de084e9f43d89c3a1d1a7247940a
出典データセット
uspto-grants-2015_07
特許番号
US09085555B2

反応ノート

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