Hydrochloric Acid → (1R,3S,5R)-2-tert-butoxycarbonyl-5-methyl-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

HRID 1527428ノート

反応式

HRID 1527428 の反応式
C([O:3][C:4]([C@@H:6]1[CH2:11][C@:10]2([CH3:12])[C@@H:8]([CH2:9]2)[N:7]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:5])C.[OH-].[K+].Cl.C(Cl)Cl>CO.C1COCC1.O>[C:16]([O:15][C:13]([N:7]1[C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][C@:10]2([CH3:12])[C@H:8]1[CH2:9]2)=[O:14])([CH3:19])([CH3:17])[CH3:18]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 68283670HCID 68283670、化合物

生成物 1

HCID 58384672(1R,3S,5R)-2-tert-butoxycarbonyl-5-methyl-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (1R,3S,5R)-5-methyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester (185 mg, 0.69 mmol) in MeOH (1.1 mL), THF (1.1 mL) and H2O (1.1 mL) was added KOH (77 mg, 1.37 mmol). The solution was stirred 2.5 h at RT, HCl (0.1N) was added (until pH 1), CH2Cl2 was added and the layers were separated (×2). The combined organic layers were dried (Na2SO4), filtered and concentrated. The material (yellow oil) thus obtained was used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.46 (m, 1H), 3.86 (m, 1H), 3.06 (m, 1H), 2.40 (dd, 1H), 1.86 (m, 1H), 1.37 (m, 9H), 1.18 (s, 3H) 0.65 (m, 2H).

後処理

  1. additionwas added
  2. customthe layers were separated (×2)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material (yellow oil) thus obtained
  7. customwas used without further purification in the next step

出典と根拠

ORDレコード
ord-4a27fc7669864962a2d908a7659c6fda
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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