Triethylamine → (2R,5R)-5-[(1S,2S)-2-(Cyclopentanecarbonylamino)-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester

HRID 20482

反応式

HRID 20482 の反応式
[CH:1]1([C:6]([OH:8])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[C:32]([O:36][C:37]([N:39]1[C@@H:44]([C@@H:45]([OH:57])[C@@H:46]([NH2:56])[CH2:47][C:48]2[CH:53]=[C:52]([F:54])[CH:51]=[C:50]([F:55])[CH:49]=2)[CH2:43][O:42][C@@H:41]([O:58][CH2:59][C:60]([CH3:63])([CH3:62])[CH3:61])[CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].C(N(CC)CC)C>ClCCl>[C:32]([O:36][C:37]([N:39]1[C@@H:44]([C@@H:45]([OH:57])[C@@H:46]([NH:56][C:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[O:8])[CH2:47][C:48]2[CH:49]=[C:50]([F:55])[CH:51]=[C:52]([F:54])[CH:53]=2)[CH2:43][O:42][C@@H:41]([O:58][CH2:59][C:60]([CH3:63])([CH3:62])[CH3:61])[CH2:40]1)=[O:38])([CH3:33])([CH3:35])[CH3:34]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 18840Cyclopentanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68560376(2R,5R)-5-[(1S,2S)-2-Amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester

生成物 1

HCID 68561969(2R,5R)-5-[(1S,2S)-2-(Cyclopentanecarbonylamino)-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester収率 98.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Stir cyclopentanecarboxylic acid (0.01 mL, 0.12 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCl) (0.02 g, 0.12 mmol) and 1-hydroxybenzotriazole monohydrate (HOBT) (0.02 g, 0.12 mmol) in dichloromethane (1 mL) at room temperature for 30 minutes. Add (2R,5R)-5-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester (0.05 g, 0.11 mmol) in dichloromethane (1 mL) and triethylamine (0.06 mL, 0.44 mmol) and stir at room temperature overnight. Wash with saturated aqueous sodium bicarbonate, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 80:20 hexane:ethyl acetate), to give the desired compound as white solid (0.06 g, 98%).

後処理

  1. washWash with saturated aqueous sodium bicarbonate
  2. dry with materialdry (magnesium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 80:20 hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-3bd97f8c08bd461d95b0c12b8c50c45e
出典データセット
uspto-grants-2010_06
特許番号
US07745438B2

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