Triethylamine → [(S)-1-(1-Pyrimidin-2-yl-cyclopropylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

HRID 1040563노트

반응식

HRID 1040563 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[N:40]1[CH:45]=[CH:44][CH:43]=[N:42][C:41]=1[C:46]1([NH2:49])[CH2:48][CH2:47]1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:10](=[O:12])[NH:49][C:46]1([C:41]2[N:42]=[CH:43][CH:44]=[CH:45][N:40]=2)[CH2:48][CH2:47]1)[CH3:13])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 85082Tert-butoxycarbonylalanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 673903101-(Pyrimidin-2-yl)cyclopropan-1-amine dihydrochloride

생성물 1

HCID 67396076[(S)-1-(1-Pyrimidin-2-yl-cyclopropylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester수율 80.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a suspension of the (S)-2-tert-Butoxycarbonylamino-propionic acid (43 mg, 0.23 mmol), HATU (99 mg, 0.26 mmol), and 1-Pyrimidin-2-yl-cyclopropylamine dihydrochloride (45 mg, 0.22 mmol) in CH2Cl2 (1.5 mL) was added triethylamine (0.12 mL, 0.87 mmol). The reaction was stirred at room temperature for 22 h, diluted with CH2Cl2 (7 mL) and then washed with saturated aqueous NaHCO3 (2×6 mL) and brine (1×6 mL). The organic phase was dried with MgSO4 and concentrated to afford 54 mg of [(S)-1-(1-Pyrimidin-2-yl-cyclopropylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester as white solid, m/z 307.56 [M+1]+.

후처리

  1. washwashed with saturated aqueous NaHCO3 (2×6 mL) and brine (1×6 mL)
  2. dry with materialThe organic phase was dried with MgSO4
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-154389db62b24dbfab6f92281d580914
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552205B2

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