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4-Toluenesulfonyl chloride → tert-butyl (3R,4R)-3-(4-tert-butoxy-benzoylamino)-4-hydroxy-azepan-1-carboxylate

HRID 1108844
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HRID 1108844 반응식
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[C:12]([O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=1)([CH3:15])([CH3:14])[CH3:13].[NH2:26][C@H:27]1[C@H:33]([OH:34])[CH2:32][CH2:31][CH2:30][N:29]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:28]1>ClCCl.CN(C)C1C=CN=CC=1.CCCCCCC>[C:12]([O:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([NH:26][C@H:27]2[C@H:33]([OH:34])[CH2:32][CH2:31][CH2:30][N:29]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:28]2)=[O:23])=[CH:24][CH:25]=1)([CH3:13])([CH3:14])[CH3:15]
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참가 물질

7

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 5353024-tert-Butoxybenzoic AcidHCID 10398972(3R,4R)-tert-Butyl 3-amino-4-hydroxyazepane-1-carboxylate

생성물 1

HCID 53982438tert-butyl (3R,4R)-3-(4-tert-butoxy-benzoylamino)-4-hydroxy-azepan-1-carboxylate

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6344
Dichloromethane
용매
3회
HCID 8900Heptane용매

실험 절차

12.91 g of p-toluenesulphonyl chloride dissolved in 15 ml of dichloromethane were added at room temperature in the course of 15 minutes to 1.94 9 of 4-(tert-butoxy)-benzoic acid and 2.63 g of 4-dimethylaminopyridine in 20 ml of dichloromethane. The reaction mixture was stirred for 2 hours and added in the course of 1 hour to 2.30 g of tert-butyl (3R,4R)-3-amino-4-hydroxy-azepan-1-carboxylate dissolved in 10 ml of dichloromethane. After stirring for 1 hour the reaction mixture was washed with 20 ml of 1N NaOH, 20 ml of 1N HCl and 20 ml of water. All aqueous phases were washed in succession with 10 ml of dichloromethane. The combined organic phases were dried over sodium sulphate, filtered and the solvent was evaporated. The foam-like residue obtained was dissolved in 80 ml of hot heptane and crystallized at room temperature overnight. The crystals were washed with 10 ml of heptane and dried to yield 3.23 g of tert-butyl (3R, 4R)-3-(4-tert-butoxy-benzoylamino)-4-hydroxy-azepan-1-carboxylate, m.p. 134-135° C.

후처리

  1. stirringAfter stirring for 1 hour the reaction mixture
  2. washwas washed with 20 ml of 1N NaOH, 20 ml of 1N HCl and 20 ml of water
  3. washAll aqueous phases were washed in succession with 10 ml of dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe foam-like residue obtained
  8. customcrystallized at room temperature overnight
  9. washThe crystals were washed with 10 ml of heptane
  10. customdried

출처 및 근거

ORD 기록
ord-5147b77abc2242998a1f1c8c327ff3cd
출처 데이터셋
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06069245

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