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

HRID 1040563ノート

反応式

HRID 1040563 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-154389db62b24dbfab6f92281d580914
出典データセット
uspto-grants-2013_10
特許番号
US08552205B2

反応ノート

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