Pyridine → Benzyl ((1S,3R)-3-carbamoylcyclohexyl)carbamate

HRID 74921

반응식

HRID 74921 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]([OH:20])=O)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:21]1C=CC=CC=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(=O)(O)[O-].[NH4+]>O1CCOCC1>[C:18]([C@@H:14]1[CH2:15][CH2:16][CH2:17][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13]1)(=[O:20])[NH2:21]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 14013Ammonium Bicarbonate2회HCID 90495Di-tert-butyl dicarbonate2회HCID 23584443rel-(1R,3S)-3-(((Phenylmethoxy)carbonyl)amino)cyclohexanecarboxylic acid2회

생성물 1

HCID 68007396Benzyl ((1S,3R)-3-carbamoylcyclohexyl)carbamate수율 91%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of (1R,3S)-3-Benzyloxycarbonylaminocyclohexanecarboxylic acid, 18c, (10.0 g, 36.1 mmol) in 1,4-dioxane (300 mL) was added pyridine (2.9 mL, 36.1 mmol), followed by di-tert-butyl dicarbonate (10.7 mL, 46.9 mmol) and ammonium bicarbonate (10.1 g, 126.2 mmol). After 3 hours, another portion of di-tert-butyl dicarbonate (1.5 g, 6.8 mmol) and ammonium bicarbonate (1.5 g, 6.8 mmol) was added and stirring was continued overnight. The reaction was quenched by addition of 2N HCl (400 mL) and stirred for 1 hour. The resulting suspension was filtered under reduced pressure, washed with 2N HCl (50 mL), water (8×50 mL) and hexanes (3×50 mL) and vacuum dried to provide benzyl N-[(1S,3R)-3-carbamoylcyclohexyl]carbamate, 18d, (9.1 g, 91%) as a white solid.

후처리

  1. waitwas continued overnight
  2. customThe reaction was quenched by addition of 2N HCl (400 mL)
  3. stirringstirred for 1 hour
  4. filtrationThe resulting suspension was filtered under reduced pressure
  5. washwashed with 2N HCl (50 mL), water (8×50 mL) and hexanes (3×50 mL) and vacuum
  6. customdried

출처 및 근거

ORD 기록
ord-771f2f8d11274aac8571533dceefdf4d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829007B2

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