Ammonium Bicarbonate → N-((1R)-1-carbamoyl-2-phenylethyl)-N-methylcarbamic acid tert.-butylester

HRID 1268629노트

반응식

HRID 1268629 반응식
[C:1]([O:5][C:6]([N:8]([C@H:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11](O)=[O:12])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])O.[NH4+].O.O[N:28]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:7])[N:8]([C@@H:10]([C:11](=[O:12])[NH2:28])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 14013Ammonium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 7015127N-Boc-N-methyl-D-phenylalanine

생성물 1

HCID 54512009N-((1R)-1-carbamoyl-2-phenylethyl)-N-methylcarbamic acid tert.-butylester수율 70.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of (2R)-2-(N-tert-butoxycarbonyl-N-methylamino)-3-phenylpropionic acid (4.00 g, 14.32 mmol) in N,N-dimethylformamide (10 ml) was cooled to 0° C. Ammonium hydrogen carbonate (5.66 g, 71.60 mmol) was added as a solid. 1-Hydroxybenzotriazole hydrate (1.94 g, 14.32 mmol) and successively N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.75 g, 14.32 mmol) were added. The suspension was stirred for 16 h, while warming up to room temperature. The reaction mixture was diluted with ethyl acetate (150 ml) and extracted with saturated sodium chloride solution/water (200 ml/300 ml). The aqueous phase was extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with saturated sodium hydrogen carbonate solution and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash-chromatography on silica (70 g), using ethyl acetate/heptane as eluent, to give 2.80 g of N-((1R)-1-carbamoyl-2-phenylethyl)-N-methylcarbamic acid tert.-butylester.

후처리

  1. extractionextracted with saturated sodium chloride solution/water (200 ml/300 ml)
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×100 ml)
  3. washThe combined organic layers were washed with saturated sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customThe crude product was purified by flash-chromatography on silica (70 g)

출처 및 근거

ORD 기록
ord-553984880d6a4cc19ee0696087b91960
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06555570B2

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