Hydrochloric Acid → N-[4-(4-bromophenoxy)benzenesulfonyl]-N-(pyridin-3-yl)methyl-D-valine hydrochloride

HRID 1594534노트

반응식

HRID 1594534 반응식
[ClH:1].C([O:6][C:7](=[O:37])[C@@H:8]([CH:34]([CH3:36])[CH3:35])[N:9]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)(C)(C)C>ClCCl>[ClH:1].[Br:33][C:30]1[CH:29]=[CH:28][C:27]([O:26][C:23]2[CH:22]=[CH:21][C:20]([S:17]([N:9]([CH2:10][C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[C@@H:8]([C:7]([OH:37])=[O:6])[CH:34]([CH3:36])[CH3:35])(=[O:19])=[O:18])=[CH:25][CH:24]=2)=[CH:32][CH:31]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 54128034HCID 54128034, 화합물

생성물 1

HCID 70089633N-[4-(4-bromophenoxy)benzenesulfonyl]-N-(pyridin-3-yl)methyl-D-valine hydrochloride

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Dry hydrogen chloride was bubbled through a −20° C. solution of N-[4-(4-bromophenoxy)benzenesulfonyl]-N-(pyridin-3-yl)methyl-D-valine t-butyl ester (920 mg, 1.6 mol) in 20 mL of dichloromethane for 10 min, and the reaction was sealed and stirred at room temperature overnight. The reaction was vented, nitrogen was bubbled through the solution for 20 min, and the solution was concentrated to give N-[4-(4-bromophenoxy)benzenesulfonyl]-N-(pyridin-3-yl)methyl-D-valine hydrochloride that was used without further purification in the next step. The above acid was dissolved in 8 mL of dichloromethane, treated with O-t-butyl hydroxylamine hydrochloride (600 mg, 4.8 mol), N-methylmorpholine (0.92 mL, 8.3 mol), and EDC (613 mg, 3.2 mol), and stirred at room temperature overnight. The reaction was partitioned between water and dichloromethane, and the organic phase was washed with brine, dried over MgSO4, and concentrated. The residue was purified by chromatography on silica, eluting with 5% methanol in dichloromethane, to give 750 mg (79%) of 2(R)-N-(tert-butoxy)-2-[4-(4-bromophenoxy)benzenesulfonyl][(pyridin-3-yl)methyl]amino-3-methylbutanamide as a clear oil.

후처리

  1. customthe reaction was sealed
  2. customnitrogen was bubbled through the solution for 20 min
  3. concentrationthe solution was concentrated

출처 및 근거

ORD 기록
ord-9c5e4e69867546bea0dd2edbc323580f
출처 데이터셋
uspto-grants-2001_09
특허 번호
USH0001992H1

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