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

HRID 1527428노트

반응식

HRID 1527428 반응식
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]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 68283670HCID 68283670, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4a27fc7669864962a2d908a7659c6fda
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085555B2

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