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1-Hydroxybenzotriazole → 3-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carbonyl-2(S)-phenylsulfonylamino-beta-alanine methyl ester

HRID 1957583
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HRID 1957583 반응식
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:23]=[C:22]([C:24]([OH:26])=O)[O:21][N:20]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[C:28]1([S:34]([NH:37][C@@H:38]([CH2:43][NH2:44])[C:39]([O:41][CH3:42])=[O:40])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)CCl.CN(C=O)C>[CH3:42][O:41][C:39](=[O:40])[C@@H:38]([NH:37][S:34]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:36])=[O:35])[CH2:43][NH:44][C:24]([C:22]1[O:21][N:20]=[C:19]([O:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:11]2[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]2)[CH:23]=1)=[O:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 190681503-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carboxylic acidHCID 22865877Methyl 3-Amino-2(S)-phenylsulfonylaminopropionate hydrochloride

생성물 1

HCID 867529453-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carbonyl-2(S)-phenylsulfonylamino-beta-alanine methyl ester
수율 72.3%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매

실험 절차

A stirred mixture of 4-5 (147 mg, 0.4 mmol), 2-9a (149 mg, 0.4 mmol), HOBT (61 mg, 0.4 mmol), DIEA (215 μL, 1.2 mmol), and DMF (6 mL) at -15° C. was treated with EDC (77 mg, 0.4 mL) followed by removal of the cooling bath. After 72 h, the reaction mixture was diluted with EtOAc and then washed with 1M NaHSO4 and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 10% acetone/CH2Cl2) gave 4-6 (176 mg) as a viscous oil. Rf 0.24 (silica, 10% acetone/CH2Cl2).

후처리

  1. customfollowed by removal of the cooling bath
  2. additionthe reaction mixture was diluted with EtOAc
  3. washwashed with 1M NaHSO4 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c675be25555043648775db5039eeaa6b
출처 데이터셋
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05786373

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