Methyl chloroformate → Methyl N-[(1R,3S)-3-benzyloxycarbonylaminocyclohexyl]carbamate

HRID 526948

반응식

HRID 526948 반응식
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3]1.Cl[C:20]([O:22][CH3:23])=[O:21].C(N(CC)CC)C>C1COCC1>[CH2:11]([O:10][C:9]([NH:8][C@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:2]([NH:1][C:20](=[O:21])[O:22][CH3:23])[CH2:3]1)=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 69756715Benzyl ((1S,3R)-3-aminocyclohexyl)carbamate2회

생성물 1

HCID 68007620Methyl N-[(1R,3S)-3-benzyloxycarbonylaminocyclohexyl]carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Benzyl N-[(1S,3R)-3-aminocyclohexyl]carbamate, 18e, (0.99 g, 3.99 mmol) was dissolved in THF (20 mL) and treated with methyl chloroformate (0.62 mL, 7.97 mmol), followed by triethylamine (1.67 mL, 11.96 mmol). After stirring for 1 hour at room temperature, the solvent was evaporated under reduced pressure and the residue was diluted into 1:3 mixture of CH2Cl2:EtOAc (130 mL) and washed with 1N HCl (50 mL) and 2N Na2CO3 (50 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the desired product, 19a, as a white solid (1.09 g, 89% yield).

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted into 1:3 mixture of CH2Cl2
  3. washEtOAc (130 mL) and washed with 1N HCl (50 mL) and 2N Na2CO3 (50 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-55bcb3c49562482bb9f7303c3618d05e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345708B2

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